936-44-7

Basic information

• Product Name: 3-PHENYLPYRROLIDINE
• Synonyms: TIMTEC-BB SBB010168;ASINEX-REAG BAS 03334576;3-PHENYLPYRROLIDINE;(Pyrrolidin-3-yl)benzene;Pyrrolidine, 3-phenyl-;3AAX-0-0
• CAS NO: 936-44-7
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.22
• Product Categories: pharmacetical;Pyrrolidine series
• Mol File: 936-44-7.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 243.36 °C at 760 mmHg
• Flash Point: 103.142 °C
• Appearance: /
• Density: 0.988 g/cm³
• Vapor Pressure: 0.0322mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 10.10±0.10(Predicted)
• CAS DataBase Reference: 3-PHENYLPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYLPYRROLIDINE(936-44-7)
• EPA Substance Registry System: 3-PHENYLPYRROLIDINE(936-44-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36-52
• Safety Statements: 26
• HazardClass: IRRITANT
• Hazardous Substances Data: 936-44-7(Hazardous Substances Data)

Usage

General Description

3-Phenylpyrrolidine is a chemical compound with the molecular formula C10H13N. It belongs to the class of organic compounds known as phenylpyrrolidines, which are pyrrolidine analogs where the pyrrolidine ring is substituted at position 3 with a phenyl group. 3-Phenylpyrrolidine is a colorless liquid with a faint odor, and it is used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. It has diverse applications in the chemical and pharmaceutical industries, serving as a building block for the production of various drugs and compounds. Overall, 3-Phenylpyrrolidine is a versatile compound with significant importance in the field of organic synthesis and pharmaceutical development.

InChI:InChI=1/C10H13N/c1-2-4-9(5-3-1)10-6-7-11-8-10/h1-5,10-11H,6-8H2

Synthetic route

4-phenyl-2,3-dihydro-1H-pyrrole (1616295-80-7) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 3h;	98%

(rac)-N-benzyl-3-phenylpyrrolidine (1026-59-1) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol	91%
With palladium on activated charcoal; ammonium formate In methanol Yield given;
With ammonium formate; palladium on activated charcoal In methanol Ambient temperature;

8-thia-9-azatricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene 8,8-dioxide (830319-60-3) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Stage #1: 8-thia-9-azatricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-8,8-dioxide With ammonia; lithium In tetrahydrofuran at -78℃; for 4.5h; Stage #2: With ammonium chloride In tetrahydrofuran at -78 - 20℃; for 16h;	90%
Stage #1: 8-thia-9-azatricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-8,8-dioxide With titanium(IV) isopropylate; chloro-trimethyl-silane; magnesium In tetrahydrofuran at 80 - 100℃; for 15h; Inert atmosphere; Stage #2: With sodium fluoride; sodium hydroxide In tetrahydrofuran; diethyl ether; water at 20℃; for 0.5h; Inert atmosphere;

tert-butyl 3-phenylpyrrolidine-1-carboxylate (147410-43-3) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Stage #1: tert-butyl 3-phenylpyrrolidine-1-carboxylate With hydrogenchloride In ethyl acetate for 2h; Stage #2: With potassium carbonate In diethyl ether; water	87%

(+-)-phenylsuccinonitrile (13706-68-8) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
With acetic acid; platinum Hydrogenation;

3-Phenyl-pyrrolidine-1-carboxylic acid methyl ester (178483-03-9) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
With hydrogenchloride In ethanol for 48h; Heating;
With hydrogenchloride In methanol Heating;

(+-)-4-phenyl-pyrrolidin-2-one → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
With sodium; butan-1-ol

phenylsuccinic acid imide → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
With sulfuric acid at 18 - 60℃; bei der elektrolytischen Reduktion;

(+-)-phenylsuccinonitrile (13706-68-8) + acetic acid (64-19-7) + platinum → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Hydrogenation;

o-bromobenzenesulfonyl chloride (2905-25-1) → 3-phenylpyrrolidine (936-44-7)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 85 percent / triethylamine / CH2Cl2 / 3 h / 0 - 20 °C 2.1: 95 percent / di(tricyclohexylphosphine)(benzylidene)ruthenium dichloride / CH2Cl2 / 15 h / 20 °C 3.1: 87 percent / Pd(OAc)2; triphenylphosphine; K2CO3 / dimethylformamide / 15 h / 110 °C 4.1: 93 percent / H2 / Pd/C / ethanol / 15 h / 20 °C 5.1: lithium; NH3 / tetrahydrofuran / 4.5 h / -78 °C 5.2: 90 percent / NH4Cl / tetrahydrofuran / 16 h / -78 - 20 °C View Scheme

8-thia-9-azatricyclo[7.2.1.02,7]dodeca-2(7),3,5,10-tetraene-8,8-dioxide (139021-60-6) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 93 percent / H2 / Pd/C / ethanol / 15 h / 20 °C 2.1: lithium; NH3 / tetrahydrofuran / 4.5 h / -78 °C 2.2: 90 percent / NH4Cl / tetrahydrofuran / 16 h / -78 - 20 °C View Scheme

1-(2-bromobenzenesulfonyl)-2,5-dihydro-1H-pyrrole (139021-59-3) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 87 percent / Pd(OAc)2; triphenylphosphine; K2CO3 / dimethylformamide / 15 h / 110 °C 2.1: 93 percent / H2 / Pd/C / ethanol / 15 h / 20 °C 3.1: lithium; NH3 / tetrahydrofuran / 4.5 h / -78 °C 3.2: 90 percent / NH4Cl / tetrahydrofuran / 16 h / -78 - 20 °C View Scheme

N,N-diallyl-2-bromobenzenesulfonamide (209543-18-0) → 3-phenylpyrrolidine (936-44-7)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: 95 percent / di(tricyclohexylphosphine)(benzylidene)ruthenium dichloride / CH2Cl2 / 15 h / 20 °C 2.1: 87 percent / Pd(OAc)2; triphenylphosphine; K2CO3 / dimethylformamide / 15 h / 110 °C 3.1: 93 percent / H2 / Pd/C / ethanol / 15 h / 20 °C 4.1: lithium; NH3 / tetrahydrofuran / 4.5 h / -78 °C 4.2: 90 percent / NH4Cl / tetrahydrofuran / 16 h / -78 - 20 °C View Scheme

phenyllithium (591-51-5) + CH3(CH2)3CH(C(O)Cl)CH2CH3 → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) CuBr*MeS2 / 1.) Et2O, cyclohexane, 0 deg C, 1 h, 2.) Et2O, cyclohexane, 0 deg C, 15 min 2: ammonium formate / 10 percent Pd/C / methanol / Ambient temperature View Scheme

iodobenzene (591-50-4) + potassium compound of l-menthol → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: i-Pr2NEt, Ag2CO3, P(o-Tol)3 / Pd(OAc)2 / dimethylformamide / 100 °C 2: HCO2NH4 / Pd/C / methanol / 4 h / Heating 3: aq. HCl / methanol / Heating View Scheme

3-Phenyl-2,3-dihydro-pyrrole-1-carboxylic acid methyl ester (178482-86-5, 200880-39-3) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCO2NH4 / Pd/C / methanol / 4 h / Heating 2: aq. HCl / methanol / Heating View Scheme
Multi-step reaction with 2 steps 1: 89 percent / HCO2NH4 / Pd/C / methanol / 4 h / Heating 2: conc. HCl (8 N) / ethanol / 48 h / Heating View Scheme

styrene (292638-84-7) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 48 percent / LDA 2: 99 percent / Me3SiI / CCl4 3: 1.) NaHCO3; 2.) t-BuOK / 1.) MeOH; 2.) t-BuOH 4: HCOONH4, 10percent Pd-C / methanol View Scheme

3-phenyl-N-(1'-tert-butoxy-2'-butyl)pyrrolidine (118988-99-1) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / Me3SiI / CCl4 2: 1.) NaHCO3; 2.) t-BuOK / 1.) MeOH; 2.) t-BuOH 3: HCOONH4, 10percent Pd-C / methanol View Scheme

3-phenyl-N-(1'-hydroxy-2'-butyl)-pyrrolidine (118989-05-2) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaHCO3; 2.) t-BuOK / 1.) MeOH; 2.) t-BuOH 2: HCOONH4, 10percent Pd-C / methanol View Scheme
Multi-step reaction with 3 steps 1: NaHCO3 / methanol / 20 °C 2: t-BuOK / 2-methyl-propan-2-ol / Heating 3: 91 percent / ammonium formate / 10percent Pd/C / methanol View Scheme

1-Benzyl-1-(1-hydroxymethyl-propyl)-3-phenyl-pyrrolidinium; bromide → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: t-BuOK / 2-methyl-propan-2-ol / Heating 2: 91 percent / ammonium formate / 10percent Pd/C / methanol View Scheme

erythro-2,3-dibromo-3-phenylpropanoic acid (6286-30-2, 31357-31-0, 54624-38-3, 91649-50-2, 99145-28-5, 113569-00-9, 113626-42-9) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: ethanolic KOH-solution 2: sulfuric acid 3: aqueous ethanol 4: platinum; acetic acid / Hydrogenation View Scheme

phenylpropynoic acid ethyl ester (2216-94-6) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous ethanol 2: platinum; acetic acid / Hydrogenation View Scheme

phenylpropyolic acid (637-44-5) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid 2: aqueous ethanol 3: platinum; acetic acid / Hydrogenation View Scheme

3-phenyl-pyrrolidine phosphoric acid salt → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
With ammonia In methanol

(+/-)-(1S,10R,11R)-epoxy-8-thia-9-azatricyclo[7.2.1.0(2,7)]dodeca-2(7),3,5-triene-8,8-dioxide → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Stage #1: (+/-)-(1S,10R,11R)-epoxy-8-thia-9-azatricyclo[7.2.1.0(2,7)]dodeca-2(7),3,5-triene-8,8-dioxide With ammonia; lithium at -78℃; Stage #2: With sodium tetrahydroborate

3-phenylpyrrolidine-2,5-dione (3464-18-4) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
With borane-THF In tetrahydrofuran at 0℃; for 3.5h; Inert atmosphere; Reflux;

phenylmagnesium bromide (100-58-3) → 3-phenylpyrrolidine (936-44-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 20 °C / Inert atmosphere 2: hydrogenchloride / water / 12 h / Reflux 3: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C View Scheme

4-nitro-8-thia-9-azatricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene 8,8-dioxide → 3-phenylpyrrolidine (936-44-7)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide / 18 h / 20 °C 2.1: Oxone / methanol / 48 h / 20 °C 3.1: magnesium; titanium(IV) isopropylate; chloro-trimethyl-silane / tetrahydrofuran / 15 h / 80 - 100 °C / Inert atmosphere 3.2: 0.5 h / 20 °C / Inert atmosphere 3.3: 15 h / 0 °C 4.1: magnesium; titanium(IV) isopropylate; chloro-trimethyl-silane / tetrahydrofuran / 15 h / 80 - 100 °C / Inert atmosphere 4.2: 0.5 h / 20 °C / Inert atmosphere View Scheme

4-(methylthia)-8-thia-9-aza-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene 8,8-dioxide → 3-phenylpyrrolidine (936-44-7)

Conditions

Yield

Multi-step reaction with 3 steps 1.1: Oxone / methanol / 48 h / 20 °C 2.1: magnesium; titanium(IV) isopropylate; chloro-trimethyl-silane / tetrahydrofuran / 15 h / 80 - 100 °C / Inert atmosphere 2.2: 0.5 h / 20 °C / Inert atmosphere 2.3: 15 h / 0 °C 3.1: magnesium; titanium(IV) isopropylate; chloro-trimethyl-silane / tetrahydrofuran / 15 h / 80 - 100 °C / Inert atmosphere 3.2: 0.5 h / 20 °C / Inert atmosphere View Scheme

3-phenylpyrrolidine (936-44-7) + 4-bromophenyl chloroformate (7693-44-9) → 4-bromophenyl 3-phenylpyrrolidine-1-carboxylate (1620228-46-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1h;	95%

3-phenylpyrrolidine (936-44-7) + 2-Chloro-N-(cyclopropylmethyl)-6-morpholinopyrimidine-4-carboxamide → (±)-N-(cyclopropylmethyl)-6-morpholino-2-(3-phenylpyrrolidin-1-yl)pyrimidine-4-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 4h; Microwave irradiation; Inert atmosphere;	95%

3-phenylpyrrolidine (936-44-7) + 4-Bromo-1-fluoro-2-nitrobenzene (364-73-8) → (±)-1-(4-bromo-2-nitrophenyl)-3-phenylpyrrolidine

Conditions	Yield
at 105℃; for 16h;	94%

3-phenylpyrrolidine (936-44-7) + 3-chloro-4'-fluoropropiophenone (347-93-3) → 1-(4-fluoro-phenyl)-3-(3-phenyl-pyrrolidin-1-yl)-propan-1-one

Conditions	Yield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide Heating;	92%

3-phenylpyrrolidine (936-44-7) + 6-(4-formylphenoxy)pyridine-3-carboxamide (676494-70-5) → (+/-)-6-[4-(3-phenyl-pyrrolidin-1-ylmethyl)-phenoxy]-nicotinamide

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 24h;	88%

3-phenylpyrrolidine (936-44-7) + 2-chloro-3-methyl-6-(pyridin-4-yl)pyrimidin-4(3H)-one (521969-44-8) → 3-methyl-2-(3-phenyl-pyrrolidin-1-yl)-6-pyridin-4-yl-3H-pyrimidin-4-one

Conditions	Yield
With triethylamine for 1h; Heating / reflux;	88%

3-phenylpyrrolidine (936-44-7) + C14H23NO6 (851000-22-1) → C24H34N2O5 (851001-08-6)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	88%

3-phenylpyrrolidine (936-44-7) + 1-iodo-propane (107-08-4) → 3-phenyl-1-propylpyrrolidine

Conditions	Yield
With potassium carbonate In acetonitrile at 50℃; for 12h;	78%

3-phenylpyrrolidine (936-44-7) + p-toluenesulfonyl chloride (98-59-9) → 1-(4-methylbenzenesulfonyl)-3-phenylpyrrolidine

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 15h;	74%
With triethylamine

3-phenylpyrrolidine (936-44-7) + bis(trichloromethyl) carbonate (32315-10-9) → 3-phenylpyrrolidine-1-carbonyl chloride

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate With pyridine In dichloromethane at -78℃; for 2h; Stage #2: 3-phenylpyrrolidine In dichloromethane at -78 - 20℃; for 1h;	73%
With triethylamine In dichloromethane at 0 - 20℃; for 2h;

3-phenylpyrrolidine (936-44-7) + 6-bromo-2-(chloromethyl)thieno[3,2-d]pyrimidin-4(3H)-one (1330782-89-2) → 6-bromo-2-[(3-phenylpyrrolidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4(3H)-one (1330783-48-6)

Conditions	Yield
With potassium carbonate; sodium iodide at 70℃; for 1h;	72%

3-phenylpyrrolidine (936-44-7) + N-[4-bromobutyl]saccharin (103564-59-6) → 1,1-dioxo-2-[4-(3-phenyl-pyrrolidin-1-yl)-butyl]-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one

Conditions	Yield
With triethylamine In acetonitrile for 12h; Heating;	66%

3-phenylpyrrolidine (936-44-7) + 5-(5-methylfuran-2-yl)-3-(methylsulfonyl)-1,2,4-triazine (1529784-81-3) → 5-(5-methylfuran-2-yl)-3-(3-phenylpyrrolidin-1-yl)-1,2,4-triazine (1529784-97-1)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	63%

3-phenylpyrrolidine (936-44-7) + 1-chloro-7-methoxy-9H-β-carboline → 1-(3-phenylpyrrolidin-1-yl)-7-methoxy-9H-β-carboline

Conditions	Yield
In neat (no solvent) at 170℃; for 24h; Sealed tube;	59%

3-phenylpyrrolidine (936-44-7) + (3-(bromomethyl)phenyl)(piperidin-1-yl)methanone (1041399-43-2) → [3-(3-phenyl-pyrrolidin-1-ylmethyl)-phenyl]-piperidin-1-yl-methanone

Conditions	Yield
With triethylamine In acetonitrile for 12h; Ambient temperature;	57%

3-phenylpyrrolidine (936-44-7) + 2,6-Dichloro-N-(cyclopropylmethyl)pyrimidine-4-carboxamide + N-Methyl-N-phenethylamine (589-08-2) → (±)-N-(cyclopropylmethyl)-2-(methyl(phenethyl)amino)-6-(3-phenylpyrrolidin-1-yl)pyrimidine-4-carboxamide

Conditions	Yield
Stage #1: 3-phenylpyrrolidine; 2,6-Dichloro-N-(cyclopropylmethyl)pyrimidine-4-carboxamide With N-ethyl-N,N-diisopropylamine In methanol at 0℃; Stage #2: N-Methyl-N-phenethylamine With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 4h; Inert atmosphere;	57%

3-phenylpyrrolidine (936-44-7) + (R)-2-(5-(3-methylureido)-2',4'-dioxo-2,3-dihydrospiro[indene-1,5'-oxazolidine]-3'-yl)acetic acid → 1-[(R)-3',5'-dioxo-4'-[2-oxo-2-(3-phenylpyrrolidin-1-yl)ethyl]-2,3-dihydrospiro[indene-1,2'-[1,4]oxazolidin]-5-yl]-3-methylurea

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h; Time;	55%

3-phenylpyrrolidine (936-44-7) + 2-bromo-1-phenyl-1-propanone (2114-00-3) + silver carbonate → (1-methyl-2-oxo-2-phenyl-ethyl) 3-phenylpyrrolidine-1-carboxylate

Conditions	Yield
In dimethyl sulfoxide at 70℃; for 0.5h;	50.4%

3-phenylpyrrolidine (936-44-7) + formaldehyd (50-00-0) + 1-prop-2-ynyl-pyrrolidin-2-one (766-61-0) → 1-[4-(3-Phenyl-pyrrolidin-1-yl)-but-2-ynyl]-pyrrolidin-2-one (137518-03-7)

Conditions	Yield
With acetic acid; copper(l) chloride In 1,4-dioxane at 50℃; for 8h;	50%

3-phenylpyrrolidine (936-44-7) + 2-(4-methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate (1159928-40-1) → 2-(4-methylpiperazin-1-yl)ethyl 3-phenylpyrrolidine-1-carboxylate (1159929-21-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h;	48%

3-phenylpyrrolidine (936-44-7) + C15H13NO4 → 4-[3-(3-phenylpyrrolidine-1-carbonyl)phenoxy]benzamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide Inert atmosphere;	42%

3-phenylpyrrolidine (936-44-7) + 2-(4-bromobutyl)-1-isoindolinone (155288-43-0) → 2-[4-(3-phenyl-pyrrolidin-1-yl)-butyl]-2,3-dihydro-isoindol-1-one

Conditions	Yield
With triethylamine In acetonitrile for 12h; Ambient temperature;	41%

3-phenylpyrrolidine (936-44-7) + 4-((2-(difluoromethoxy)benzyl)(2-(methylamino)-2-oxoethyl)carbamoyl)-1H-pyrrole-2-carboxylic acid → N-(2-(difluoromethoxy)benzyl)-N-(2-(methylamino)-2-oxoethyl)-2-(3-phenylpyrrolidine-1-carbonyl)-1H-imidazole-5-carboxamide

Conditions	Yield
Stage #1: 4-((2-(difluoromethoxy)benzyl)(2-(methylamino)-2-oxoethyl)carbamoyl)-1H-pyrrole-2-carboxylic acid With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.5h; Stage #2: 3-phenylpyrrolidine In N,N-dimethyl-formamide at 20℃; for 16h;	36%

3-phenylpyrrolidine (936-44-7) + phenyl 2-(5-chloro-1H-indol-3-yl)ethylcarbamate (1258503-69-3) → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-phenylpyrrolidine-1-carboxamide (1258502-26-9)

Conditions	Yield
Stage #1: 3-phenylpyrrolidine With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.0833333h; Stage #2: phenyl 2-(5-chloro-1H-indol-3-yl)ethylcarbamate In tetrahydrofuran; mineral oil at 20℃;	35%

3-phenylpyrrolidine (936-44-7) + 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (1369487-49-9) → (1-(4-chlorobenzyl)-1H-indol-2-yl)(4-(3-phenylpyrrolidine-1-carbonyl)piperidin-1-yl)methanone (1401619-02-0)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 36h;	32%

3-phenylpyrrolidine (936-44-7) + 7-chloro-3-(cyclopropylmethyl)-8-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine (1254981-30-0) → 3-(cyclopropylmethyl)-7-(3-phenyl-1-pyrrolidinyl)-8-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyridine (1254979-16-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 180℃; for 0.333333h; Microwave irradiation;	32%

Upstream product

• 13706-68-8 (+-)-phenylsuccinonitrile 
• 1026-59-1 (rac)-N-benzyl-3-phenylpyrrolidine 
• 178483-03-9 3-Phenyl-pyrrolidine-1-carboxylic acid methyl ester 
• 64-19-7 acetic acid 
• 830319-60-3 8-thia-9-azatricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene-8,8-dioxide 
• 147410-43-3 tert-butyl 3-phenylpyrrolidine-1-carboxylate 
• 2905-25-1 o-bromobenzenesulfonyl chloride 
• 139021-60-6 8-thia-9-azatricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5,10-tetraene-8,8-dioxide 
• 139021-59-3 1-(2-bromobenzenesulfonyl)-2,5-dihydro-1H-pyrrole 
• 209543-18-0 N,N-diallyl-2-bromobenzenesulfonamide 
• 591-51-5 phenyllithium 
• 591-50-4 iodobenzene 
• 178482-86-5 3-Phenyl-2,3-dihydro-pyrrole-1-carboxylic acid methyl ester 
• 100-42-5 styrene 

Downstream Products

• 137518-03-7 1-[4-(3-Phenyl-pyrrolidin-1-yl)-but-2-ynyl]-pyrrolidin-2-one 
• 442911-07-1 7-[(3-phenylpyrrolidin-1-yl)carbonyl]-1,6-naphthyridin-8-ol 
• 1330783-48-6 6-bromo-2-[(3-phenylpyrrolidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4(3H)-one 
• 20948-37-2 3'-phenyl-5,7-dihydro-spiro[[1,3]dioxolo[4,5-f]isoindolium-6,1'-pyrrolidinium]; iodide 
• 20948-36-1 3'-phenyl-2,3,5,7-tetrahydro-spiro[furo[2,3-f]isoindolium-2,1'-pyrrolidinium]; iodide 
• 33743-96-3 proroxan 

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