5554-64-3

Basic information

• Product Name: 3-dimethylamino-1-phenyl-propan-1-ol
• Synonyms: 1-Phenyl-3-(dimethylamino)-1-propanol;3-(Dimethylamino)-1-phenyl-1-propanol;USAF EL-80;α-[2-(Dimethylamino)ethyl]benzenemethanol;1-Propanol, 3-dimethylamino-1-phenyl-;BenzeneMethanol, a-[2-(diMethylaMino)ethyl]-;N,N-Dimethyl-3-hydroxy-3-phenylpropylamine;3-(DIMETHYLAMINO)-1-PHENYLPROPAN-1-OL(WXG00975)
• CAS NO: 5554-64-3
• Molecular Formula: C₁₁H₁₇NO
• Molecular Weight: 179.258780
• Mol File: 5554-64-3.mol
• Article Data: 26

Chemical Properties

• Melting Point: 47-48℃
• Boiling Point: 128-130℃ (3 Torr)
• Flash Point: 99.8 °C
• Appearance: /
• Density: 1.011 g/cm³
• Storage Temp.: 2-8°C
• PKA: 14.21±0.20(Predicted)
• CAS DataBase Reference: 3-dimethylamino-1-phenyl-propan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-dimethylamino-1-phenyl-propan-1-ol(5554-64-3)
• EPA Substance Registry System: 3-dimethylamino-1-phenyl-propan-1-ol(5554-64-3)

Safety Data

• Hazardous Substances Data: 5554-64-3(Hazardous Substances Data)

Usage

Uses

3-Dimethylamino-1-phenyl-1-propanol is a useful synthetic intermediate. It can be used to prepare phenoxyphenyl diamine-based histamine H3 antagonists with serotonin reuptake inhibitor activities. It is also used to synthesize indolyl aryl propanamines as dual acting norepinephrine and serotonin reuptake inhibitors.

Synthetic route

3-(dimethylamino)propiophenone hydrochloride (879-72-1) → N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3)

Conditions	Yield
With methanol; sodium tetrahydroborate; sodium hydroxide at 20℃; for 1h; pH=12 - 13; Cooling with ice;	96%
Stage #1: 3-(dimethylamino)propiophenone hydrochloride With potassium hydroxide In water Stage #2: With methanol; sodium tetrahydroborate; potassium hydroxide at 0 - 22℃; for 1.5h;	95%
With diisobutylaluminium hydride In tetrahydrofuran; dichloromethane for 2h; Ambient temperature;	92%

3-dimethylaminopropiophenone (3506-36-3) → N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3)

Conditions	Yield
With sodium tetrahydroborate In water at 0 - 20℃;	91%
With lithium aluminium tetrahydride
With aluminium trichloride; aluminum isopropoxide; isopropyl alcohol

N,N-Dimethyl-α-chlorobenzoylacetamide (87968-05-6) → N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) + (+/-)-N-methylephedrine (1201-56-5)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 20h; Heating;	A n/a B 24%

3-chloro-1-phenyl-propan-1-ol (18776-12-0) + dimethyl amine (124-40-3) → N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3)

styrene (292638-84-7) + N-(chloromethyl)dimethylamine (30438-74-5) → 2-benzyl-2-propenal (30457-88-6) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) + methyl-(3-phenyl-propyl)-amine (23580-89-4) + bis-(3-phenyl-propyl)-amine (93948-20-0)

Conditions	Yield
In acetonitrile for 12h; Heating; Yield given. Further byproducts given. Yields of byproduct given;

diethyl ether (60-29-7) + water (7732-18-5) + 3-dimethylaminopropiophenone (3506-36-3) + activated aluminium → N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) + 1.6-bis-dimethylamino-3.4-diphenyl-hexanediol-(3.4)

β-dimethylamino-propiophenone hydrochloride → N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3)

Conditions	Yield
With water; palladium Hydrogenation;

3-dimethylamino-1-phenyl-propanone-(1)-hydrochloride → N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3)

Conditions	Yield
With water; nickel Hydrogenation;

3-(dimethylamino)propiophenone hydrochloride (879-72-1) + water (7732-18-5) + palladium/charcoal → N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3)

Conditions	Yield
Hydrogenation;

acetophenone (98-86-2) → N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / aq. HCl / ethanol / 2 h / Heating 2: 91 percent / NaBH4 / H2O / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol; water / 3 h / Heating / reflux 2: sodium tetrahydroborate / ethanol / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: hydrogenchloride / ethanol / 2 h / Reflux 2.1: potassium hydroxide / water 2.2: 1.5 h / 0 - 22 °C View Scheme

acetophenone (98-86-2) + butadiynediyl-bis magnesium bromide → N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / conc. aq. HCl / ethanol / 2 h / Heating 2: 92 percent / DIBAL-H / tetrahydrofuran; CH2Cl2 / 2 h / Ambient temperature View Scheme

N,N-dimethyl 3-oxo-3-phenyl-propanamide (18871-71-1) → N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / N-chlorosuccinimide / CCl4 / 4 h / Heating 2: LiAlH4 / diethyl ether / 20 h / Heating View Scheme

3-(N,N-dimethylamino)propiophenone → N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3)

Conditions	Yield
With sodium borohydrid In methanol; water; isopropyl alcohol	15.2 g (97%)

N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → 3-(dimethylamino)-1-phenylpropyl chloride hydrochloride (1011-59-2)

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With hydrogenchloride In diethyl ether Stage #2: With thionyl chloride Reflux;	96%
With hydrogenchloride; thionyl chloride In dichloromethane
With thionyl chloride In dichloromethane

5-bromo-2-chloropyridine (53939-30-3) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → 3-((5-bromopyridin-2-yl)oxy)-N,N-dimethyl-3-phenylpropan-1-amine (1584114-08-8)

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Stage #2: 5-bromo-2-chloropyridine In N,N-dimethyl-formamide; mineral oil at 75℃; for 12h;	91%

4-nitro-1H-pyrazole (2075-46-9) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → N,N-dimethyl-3-(4-nitro-1H-pyrazol-1-yl)-3-phenylpropan-1-amine (1557241-82-3)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;	80%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement;

4-nitro-phenol (100-02-7) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → N,N-dimethyl-3-(4-nitrophenoxy)-3-phenylpropan-1-amine (72084-00-5)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; Mitsunobu Displacement;	80%
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 48h; Mitsunobu Displacement;

N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) + 6-[1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]-1-(2-trimethylsilanylethoxymethyl)-1H-indazole-3-carboxylic acid (1H-pyrazol-4-yl)amide (1422982-35-1) → C36H48N8O3Si

Conditions	Yield
With tributylphosphine; diethylazodicarboxylate In tetrahydrofuran at 70℃; for 1h;	75%

1-indoline (496-15-1) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → N-[3-(2,3-dihydro-1H-indol-1-yl)-3-phenylpropyl]-N,N-dimethylamine (915953-59-2)

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 1-indoline With potassium carbonate at 20℃; for 14h; Further stages.;	72%

N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) + phenol (108-95-2) → N,N-dimethyl-3-phenoxy-3-phenyl-1-propanamine

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile Stage #2: phenol With potassium carbonate In acetonitrile for 65h; Heating;	69%

3,4-dimethoxyphenol (2033-89-8) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → [3-(3,4-dimethoxy-phenoxy)-3-phenyl-propyl]-dimethyl-amine

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 3,4-dimethoxyphenol With potassium carbonate In acetonitrile for 16h; Heating;	67%

6-fluoroindoline (2343-23-9) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → C19H23N2F (915953-62-7)

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 6-fluoroindoline With potassium carbonate at 20℃; for 14h; Further stages.;	64%

N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → 3-chloro-N,N-dimethyl-3-phenylpropan-1-amine (79130-51-1)

Conditions	Yield
With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃;	64%

N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) + 2-fluoro-1,4-dimethoxybenzene (82830-49-7) → [3-(2,5-dimethoxy-phenoxy)-3-phenylpropyl]dimethylamine (1342798-05-3)

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 2-fluoro-1,4-dimethoxybenzene In dimethyl sulfoxide at 135 - 140℃; for 4h;	63%

6-chloropyridine-3-ol (41288-96-4) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → 3-((6-chloropyridin-3-yl)oxy)-N,N-dimethyl-3-phenylpropan-1-amine (1584114-00-0)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement; Inert atmosphere;	60%

N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) + 2,3-dihydro-4-fluoro-1H-indole (552866-98-5) → C19H23N2F (915953-60-5)

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 2,3-dihydro-4-fluoro-1H-indole With potassium carbonate at 20℃; for 14h; Further stages.;	51%

5-fluoroindoline (2343-22-8) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → C19H23N2F (915953-61-6)

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 5-fluoroindoline With potassium carbonate at 20℃; for 14h; Further stages.;	49%

2,3-dihydro-7-fluoro-1H-indole (769966-04-3) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → C19H23N2F (915953-63-8)

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 2,3-dihydro-7-fluoro-1H-indole With potassium carbonate at 20℃; for 14h; Further stages.;	47%

O-methylresorcine (150-19-6) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → [3-(3-methoxy-phenoxy)-3-phenyl-propyl]-dimethyl-amine (57226-14-9)

Conditions	Yield
With PS-PPh3; dibenzyl azodicarboxylate In dichloromethane at 20℃; for 20h; Mitsunobu reaction;	47%

4-fluorobenzo[1,3]dioxolane (943830-74-8) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) + oxalic acid (144-62-7) → 3-[(benzo[d][1,3]dioxolan-4-yl)oxy]-N,N-dimethyl-3-phenylpropylamine oxalate

Conditions	Yield
Stage #1: 4-fluorobenzo[1,3]dioxolane; N,N-dimethyl-3-hydroxy-3-phenylpropylamine With potassium hydroxide In dimethyl sulfoxide at 85℃; for 4h; Stage #2: oxalic acid	47%

N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) + 4-methoxy-phenol (150-76-5) → N,N-dimethyl-3-(4-methoxy-phenyloxy)-3-phenyl-propanamine

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 4-methoxy-phenol With potassium carbonate In acetonitrile for 16h; Heating;	46%

4-hydroxybenzotrifluoride (402-45-9) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → N,N-dimethyl-3-phenyl-3-(4-(trifluoromethyl)phenoxy)-1-propylamine (56225-81-1)

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 4-hydroxybenzotrifluoride With potassium carbonate In acetonitrile for 16h; Heating;	35%

4-(3-piperidin-1-yl-propoxy)-phenol (81878-15-1) + N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → dimethyl-{3-phenyl-3-[4-(3-piperidin-1-yl-propoxy)-phenoxy]-propyl}-amine

Conditions	Yield
With PS-PPh3; dibenzyl azodicarboxylate In dichloromethane at 20℃; for 20h; Mitsunobu reaction;	10%

N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) + 2-chloro-2,2-diphenylacetyl chloride (2902-98-9) → benzilic acid-(3-dimethylamino-1-phenyl-propyl ester) (801171-59-5)

Conditions	Yield
With diethyl ether Erhitzen des Reaktionsprodukts mit Wasser;

N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) → benzoic acid-(3-dimethylamino-1-phenyl-propyl ester) (25314-81-2)

Conditions	Yield
With benzoyl chloride In 1,4-dioxane at 25 - 50℃; Kinetics;

N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) + benzoyl chloride (98-88-4) → benzoic acid-(3-dimethylamino-1-phenyl-propyl ester) (25314-81-2)

Conditions	Yield
In benzene

N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) + methyl iodide (74-88-4) → 3-Hydroxy-3-phenylpropyltrimethylammoniumiodid (24221-52-1)

Conditions	Yield
In ethanol for 0.666667h; Heating; Yield given;

N,N-dimethyl-3-hydroxy-3-phenylpropylamine (5554-64-3) + (R)-Mandelic Acid (611-71-2) → (R)-3-Dimethylamino-1-phenyl-propan-1-ol; compound with (R)-hydroxy-phenyl-acetic acid

Conditions	Yield
In ethyl acetate 77 deg C, 1 h and -15 deg C, 1 h; Yield given;

Upstream product

• 879-72-1 3-(dimethylamino)propiophenone hydrochloride 
• 7732-18-5 water 
• 98-86-2 acetophenone 
• 1201-93-0 1-phenyl-3-dimethylaminoprop-2-enone 
• 3623-15-2 phenyl propargyl ketone 
• 100-52-7 benzaldehyde 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 18871-71-1 N,N-dimethyl 3-oxo-3-phenyl-propanamide 
• 60-29-7 diethyl ether 
• 3506-36-3 3-dimethylaminopropiophenone 
• 100-42-5 styrene 
• 30438-74-5 N-(chloromethyl)dimethylamine 
• 87968-05-6 N,N-Dimethyl-α-chlorobenzoylacetamide 
• 18776-12-0 3-chloro-1-phenyl-propan-1-ol 

Downstream Products

• 801171-59-5 benzilic acid-(3-dimethylamino-1-phenyl-propyl ester) 
• 56225-81-1 N,N-dimethyl-3-phenyl-3-(4-(trifluoromethyl)phenoxy)-1-propylamine 
• 40116-79-8 (R)-(+)-3-(dimethylamino)-1-phenylpropan-1-ol 
• 36296-97-6 (S)-3-(dimethylamino)-1-phenylpropan-1-ol 
• 83015-25-2 N,N-dimethyl-3-(2-methyl-phenyloxy)-3-phenyl-propanamine 
• 1557241-78-7 1-(3-(dimethylamino)-1-phenylpropyl)-1H-pyrazol-4-amine 
• 1557241-82-3 N,N-dimethyl-3-(4-nitro-1H-pyrazol-1-yl)-3-phenylpropan-1-amine 
• 5424-50-0 NSC 12229 
• 1011-59-2 3-(dimethylamino)-1-phenylpropyl chloride hydrochloride 
• 915953-79-6 C₁₈H₁₉FN₂ 
• 915953-78-5 C₁₈H₁₉FN₂ 
• 871348-68-4 1[3-(1H-indol-1-yl)-3-phenyl-propyl]-methyl-amine 
• 915953-81-0 C₁₈H₁₉FN₂ 
• 915953-80-9 C₁₈H₁₉FN₂ 

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