28075-29-8

Basic information

• Product Name: N-Methyl-3,3-diphenylpropylamine
• Synonyms: (3,3-diphenylpropyl)methylamine;N-METHYL-3,3-DIPHENYLPROPYLAMINE;3,3-Diphenyl-N-Methylpropylamine;Methyl(3,3-diphenylpropyl)amine;N-Methyl-3,3-diphenyl-1-propanamine;N-Methyl-γ-phenylbenzenepropan-1-amine;3,3-Diphenyl-N-diphenyl-N-methylpropylamine;N-Methyl-3,3-diphenylpropan-1-aMine
• CAS NO: 28075-29-8
• Molecular Formula: C₁₆H₁₉N
• Molecular Weight: 225.33
• EINECS: 248-821-5
• Mol File: 28075-29-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 347.374 °C at 760 mmHg
• Flash Point: 164.5 °C
• Appearance: /
• Density: 0.989 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 10.48±0.10(Predicted)
• CAS DataBase Reference: N-Methyl-3,3-diphenylpropylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-3,3-diphenylpropylamine(28075-29-8)
• EPA Substance Registry System: N-Methyl-3,3-diphenylpropylamine(28075-29-8)

Safety Data

• Hazardous Substances Data: 28075-29-8(Hazardous Substances Data)

Usage

Uses

N-Methyl-3,3-diphenylpropylamine is an intermediate for the synthesis of SNRI-NMDA antagonist and neuroprotectants.

InChI:InChI=1/C17H21N/c1-18-14-8-13-17(15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17-18H,8,13-14H2,1H3

Synthetic route

3-methylamino-1-phenylpropan-1-ol (42142-52-9) + benzene (71-43-2) → N-methyl-3,3-diphenylpropylamine (28075-29-8)

Conditions	Yield
With trifluorormethanesulfonic acid	83%

3,3-diphenylpropanoic acid N-methylamide (348607-76-1) → N-methyl-3,3-diphenylpropylamine (28075-29-8)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 4h;	66%

N-benzyl-N-methyl-3,3-diphenylpropylamine → N-methyl-3,3-diphenylpropylamine (28075-29-8)

Conditions	Yield
With hydrogenchloride; aq. NaOH In methanol

benzyl-methyl-amine (103-67-3) → N-methyl-3,3-diphenylpropylamine (28075-29-8)

Cinnamic acid (621-82-9) → N-methyl-3,3-diphenylpropylamine (28075-29-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / Heating 2: 1,4-dioxane / 0.17 h / 20 °C 3: trifluorormethanesulfonic acid / 2 h / 20 °C 4: lithium aluminium tetrahydride / diethyl ether / 4 h View Scheme

cinnamoyl chloride (102-92-1) → N-methyl-3,3-diphenylpropylamine (28075-29-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,4-dioxane / 0.17 h / 20 °C 2: trifluorormethanesulfonic acid / 2 h / 20 °C 3: lithium aluminium tetrahydride / diethyl ether / 4 h View Scheme

4-methylcinnamoyl chloride (13565-07-6, 15851-89-5) → N-methyl-3,3-diphenylpropylamine (28075-29-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,4-dioxane / 0.17 h / 20 °C 2: trifluorormethanesulfonic acid / 1 h / 20 °C 3: lithium aluminium tetrahydride / diethyl ether / 4 h View Scheme

C11H11ClO → N-methyl-3,3-diphenylpropylamine (28075-29-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,4-dioxane / 0.17 h / 20 °C 2: trifluorormethanesulfonic acid / 1 h / 20 °C 3: lithium aluminium tetrahydride / diethyl ether / 4 h View Scheme

4-methylcinnamic acid (1866-39-3) → N-methyl-3,3-diphenylpropylamine (28075-29-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / Heating 2: 1,4-dioxane / 0.17 h / 20 °C 3: trifluorormethanesulfonic acid / 1 h / 20 °C 4: lithium aluminium tetrahydride / diethyl ether / 4 h View Scheme

3-(3,4-Dimethylphenyl)-propensaeure (147219-20-3, 60521-25-7) → N-methyl-3,3-diphenylpropylamine (28075-29-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / Heating 2: 1,4-dioxane / 0.17 h / 20 °C 3: trifluorormethanesulfonic acid / 1 h / 20 °C 4: lithium aluminium tetrahydride / diethyl ether / 4 h View Scheme

N-methylcinnamamide (2757-10-0) → N-methyl-3,3-diphenylpropylamine (28075-29-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluorormethanesulfonic acid / 2 h / 20 °C 2: lithium aluminium tetrahydride / diethyl ether / 4 h View Scheme

3-(4-methylphenyl)propenoic acid N-methylamide → N-methyl-3,3-diphenylpropylamine (28075-29-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluorormethanesulfonic acid / 1 h / 20 °C 2: lithium aluminium tetrahydride / diethyl ether / 4 h View Scheme

N-methyl-3,3-diphenylpropylamine (28075-29-8) + methyl vinyl ketone (78-94-4) → 4-[N-(3,3-diphenylpropyl)-N-methylamino]-2-butanone (100427-47-2)

Conditions	Yield
In diethyl ether at -5 - 3℃;	90%

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-β-chloroethyl ester 5-isopropyl ester (54851-30-8) → 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-ethyl} ester 5-isopropyl ester

Conditions	Yield
Heating;	85%

3-chloro-2-methylpropan-2-ol (558-42-9) + N-methyl-3,3-diphenylpropylamine (28075-29-8) → 2,N-dimethyl-N-(3,3-diphenylpropyl)-1-amino-2-propanol (100442-33-9)

Conditions	Yield
In xylene for 8.5h; Heating;	80%

N-methyl-3,3-diphenylpropylamine (28075-29-8) + methyloxirane (75-56-9, 16033-71-9) → 1-[N-(3,3-diphenylpropyl)-N-methylamino]-2-propanol (100427-50-7)

Conditions	Yield
In methanol at 15 - 20℃; for 96h;	70%

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-chloro-ethyl) ester 5-(2-propoxy-ethyl) ester (100427-03-0) → 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-ethyl} ester 5-(2-propoxy-ethyl) ester

Conditions	Yield
Heating;	59%

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 2-chloroethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-ethoxy-carbonyl-1,4-dihydropyridine-3-carboxylate (54585-92-1) → 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-ethyl} ester 5-ethyl ester

Conditions	Yield
Heating;	55%

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 3-(3-chloropropyl)-1,3-dihydro-7,8-dimethoxy-2H-3-benzazepine-2-one (85175-59-3) → 7,8-dimethoxy-3-aminopropyl-1,3-dihydro-2H-3-benzazepin-2-one

Conditions	Yield
In toluene for 10h; Heating;	50%

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-chloro-ethyl) ester 5-isobutyl ester (91040-32-3) → 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-ethyl} ester 5-isobutyl ester

Conditions	Yield
Heating;	50%

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 4-Nitrophenyl chloroformate (7693-46-1) → 4-nitrophenyl 3,3-diphenylpropyl(methyl)carbamate

Conditions	Yield
With triethylamine In dichloromethane for 2h; Inert atmosphere;	49%

N-methyl-3,3-diphenylpropylamine (28075-29-8) + (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester → (R)-1-(2-(N-(3,3-diphenyl-1-propyl)-N-methylamino)ethyl)-3-piperidinecarboxylic acid ethyl ester

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 504000h; Condensation;	36%

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-chloro-1-methyl-ethyl) ester 5-methyl ester → 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-1-methyl-ethyl} ester 5-methyl ester

Conditions	Yield
Heating;	35%

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 3-chloropropyl ester (91116-19-7) → 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{3-[(3,3-diphenyl-propyl)-methyl-amino]-propyl} ester 5-methyl ester

Conditions	Yield
Heating;	35%

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-chloro-1-methyl-ethyl) ester 5-isobutyl ester (100427-02-9) → 4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-1-methyl-ethyl} ester 5-isobutyl ester

Conditions	Yield
Heating;	5%

(6-bromo-hexyl)-diethyl-amine (74509-66-3) + N-methyl-3,3-diphenylpropylamine (28075-29-8) → N-(3,3-Diphenyl-propyl)-N',N'-diethyl-N-methyl-hexane-1,6-diamine (103044-09-3)

Conditions	Yield
With sodium carbonate In ethanol

5-bromopentan-1-nitrile (5414-21-1) + N-methyl-3,3-diphenylpropylamine (28075-29-8) → 5-[(3,3-Diphenyl-propyl)-methyl-amino]-pentanenitrile (102470-42-8)

Conditions	Yield
With sodium carbonate In ethanol

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 2-chloroethyl ester (100427-00-7) → 4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-ethyl} ester 5-methyl ester

Conditions	Yield
Heating; Yield given;

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-chloroethyl)ester-5-methyl ester (92130-26-2) → 2,6-Dimethyl-4-(2-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-ethyl} ester 5-methyl ester

Conditions	Yield
Heating; Yield given;

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 4-Benzo[1,2,5]oxadiazol-4-yl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-chloro-ethyl) ester 5-methyl ester (100427-01-8) → 4-Benzo[1,2,5]oxadiazol-4-yl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-ethyl} ester 5-methyl ester

Conditions	Yield
Heating; Yield given;

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(4-bromo-butyl) ester 5-methyl ester → 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{4-[(3,3-diphenyl-propyl)-methyl-amino]-butyl} ester 5-methyl ester

Conditions	Yield
In N,N-dimethyl-formamide for 16h; Ambient temperature; Yield given;

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-chloroethyl)ester-5-methyl ester (54527-89-8) → 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-ethyl} ester 5-methyl ester

Conditions	Yield
Heating; Yield given;

N-methyl-3,3-diphenylpropylamine (28075-29-8) + 2-chloro-6,7-dimethoxyquinazolin-4-amine (23680-84-4) → N2-(3,3-diphenyl-propyl)-6,7-dimethoxy-N2-methyl-quinazoline-2,4-diamine

Conditions	Yield
In i-Amyl alcohol for 5h; Heating;

N-methyl-3,3-diphenylpropylamine (28075-29-8) → (R)-1-{2-[(3,3-Diphenyl-propyl)-methyl-amino]-ethyl}-piperidine-3-carboxylic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: 36 percent / K2CO3 / acetone / 504000 h / 20 °C 2: aq. NaOH / ethanol / 20 °C View Scheme

N-methyl-3,3-diphenylpropylamine (28075-29-8) → lercanidipine (100427-26-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / xylene / 8.5 h / Heating 2: 72 percent / toluene / 2 h / 80 °C 3: 91 percent / HCl / CHCl3 / 15 °C 4: propan-2-ol / Heating View Scheme
Multi-step reaction with 2 steps 1: 80 percent / xylene / 8.5 h / Heating 2: dimethylformamide; CH2Cl2 / 3 h / 0 °C View Scheme

N-methyl-3,3-diphenylpropylamine (28075-29-8) → 4-[N-(3,3-diphenylpropyl)-N-methylamino]-2-butanol

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / diethyl ether / -5 - 3 °C 2: 83 percent / NaBH4 / methanol / 0.08 h / 0 °C View Scheme

N-methyl-3,3-diphenylpropylamine (28075-29-8) → 1,1,N-trimethyl-N-(3,3-diphenylpropy)-2-aminoethyl acetoacetate (100427-51-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / xylene / 8.5 h / Heating 2: 72 percent / toluene / 2 h / 80 °C View Scheme

N-methyl-3,3-diphenylpropylamine (28075-29-8) → 3-Oxo-butyric acid 2-[(3,3-diphenyl-propyl)-methyl-amino]-1-methyl-ethyl ester (100427-52-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / methanol / 96 h / 15 - 20 °C 2: 68 percent / toluene / 95 °C View Scheme

N-methyl-3,3-diphenylpropylamine (28075-29-8) → 2-[1-(2,3-Dichloro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid 2-[(3,3-diphenyl-propyl)-methyl-amino]-1-methyl-ethyl ester (210579-46-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / methanol / 96 h / 15 - 20 °C 2: 68 percent / toluene / 95 °C 3: 93 percent / HCl / CHCl3 / 24 h / Ambient temperature View Scheme

Upstream product

• 42142-52-9 3-methylamino-1-phenylpropan-1-ol 
• 71-43-2 benzene 
• 2757-10-0 N-methylcinnamamide 
• 147219-20-3 3-(3,4-Dimethylphenyl)-propensaeure 
• 1866-39-3 4-methylcinnamic acid 
• 13565-07-6 4-methylcinnamoyl chloride 
• 102-92-1 cinnamoyl chloride 
• 621-82-9 Cinnamic acid 
• 348607-76-1 3,3-diphenylpropanoic acid N-methylamide 
• 103-67-3 benzyl-methyl-amine 

Downstream Products

• 102470-42-8 5-[(3,3-Diphenyl-propyl)-methyl-amino]-pentanenitrile 
• 100442-33-9 2,N-dimethyl-N-(3,3-diphenylpropyl)-1-amino-2-propanol 
• 100427-47-2 4-[N-(3,3-diphenylpropyl)-N-methylamino]-2-butanone 
• 100427-26-7 lercanidipine 
• 100427-51-8 1,1,N-trimethyl-N-(3,3-diphenylpropy)-2-aminoethyl acetoacetate 
• 100427-52-9 3-Oxo-butyric acid 2-[(3,3-diphenyl-propyl)-methyl-amino]-1-methyl-ethyl ester 
• 210579-46-7 2-[1-(2,3-Dichloro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid 2-[(3,3-diphenyl-propyl)-methyl-amino]-1-methyl-ethyl ester 
• 210579-45-6 2-[1-(3-Nitro-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid 2-[(3,3-diphenyl-propyl)-methyl-amino]-1,1-dimethyl-ethyl ester 

Relevant articles and documents

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