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Chemical Structure| 100442-33-9 Chemical Structure| 100442-33-9
Chemical Structure| 100442-33-9

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Product Details of 1-[(3,3-Diphenylpropyl)methylamino]-2-methyl-2-propanol

CAS No. :100442-33-9
Formula : C20H27NO
M.W : 297.43
SMILES Code : C1(=CC=CC=C1)C(CCN(C)CC(C)(O)C)C2=CC=CC=C2
MDL No. :MFCD07782118
Boiling Point : No data available
InChI Key :MQWDISMNBYOLAB-UHFFFAOYSA-N
Pubchem ID :10851563

Safety of 1-[(3,3-Diphenylpropyl)methylamino]-2-methyl-2-propanol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of 1-[(3,3-Diphenylpropyl)methylamino]-2-methyl-2-propanol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 100442-33-9 ]

[ 100442-33-9 ] Synthesis Path-Downstream   1~17

  • 1
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  • [ 558-42-9 ]
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  • 3
  • [ 88712-56-5 ]
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  • 4
  • [ 100442-33-9 ]
  • 5-Chlorocarbonyl-2,6-dimethyl-4-(4-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester [ No CAS ]
  • 2,6-Dimethyl-4-(4-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-1,1-dimethyl-ethyl} ester 5-methyl ester [ No CAS ]
  • 5
  • [ 100442-33-9 ]
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  • 6
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  • [ 210579-45-6 ]
  • 7
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  • 2-[1-(2,3-Dichloro-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid 2-[(3,3-diphenyl-propyl)-methyl-amino]-1,1-dimethyl-ethyl ester; hydrochloride [ No CAS ]
  • 8
  • [ 100442-33-9 ]
  • 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(1,1-dimethyl-2-propoxy-ethyl) ester 5-{2-[(3,3-diphenyl-propyl)-methyl-amino]-1,1-dimethyl-ethyl} ester [ No CAS ]
  • 9
  • [ 100442-33-9 ]
  • 4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-1,1-dimethyl-ethyl} ester 5-methyl ester [ No CAS ]
  • 10
  • [ 100442-33-9 ]
  • 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-1,1-dimethyl-ethyl} ester 5-ethyl ester [ No CAS ]
  • 11
  • [ 100442-33-9 ]
  • 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-1,1-dimethyl-ethyl} ester 5-isopropyl ester [ No CAS ]
  • 12
  • [ 100442-33-9 ]
  • 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-1,1-dimethyl-ethyl} ester 5-(2-propoxy-ethyl) ester [ No CAS ]
  • 13
  • [ 75-77-4 ]
  • [ 100442-33-9 ]
  • 2,N-dimethyl-2-(trimethylsilyloxy)-N-(3,3-diphenylpropyl)-1-propanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 10 - 30℃;Inert atmosphere; 2,N-Dimethyl-N-(3,3-diphenylpropyl)-1-amino-2-propanol (5.0 gm) is dissolved in methylene chloride (25 ml) at 25-30 C., triethylamine (2.5 gm) is added and then the contents are cooled to 10-15 C. under N2 atmosphere. Trimethylsilyl chloride (2.5 gm) is slowly added to the reaction mass while maintaining the temperature in between 10-15 C., the mass temperature is raised to 25-30 C. and maintain for 2 hours at the same temperature to give the reaction mass having 2,N-dimethyl-2-(trimethylsilyloxy)-N-(3,3-diphenylpropyl)-1-propanamine.
With triethylamine; In dichloromethane; at 10 - 30℃; for 2.0h; Step-ll; 2,N-Dimethyl-N-(3,3-diphenylpropyI)-1-amino-2-propanol (5.0 gm) is dissolved in methylene chloride (25 ml) at 25 - 300C, triethylamine (2.5 gm) is added and then the contents are cooled to 10 - 150C under N2 atmosphere. Trimethylsilyl chloride (2.5 gm) is slowly added to the reaction mass while maintaining the temperature in between 10 - 150C, the mass temperature is raised to 25 - 300C and maintain for 2 hours at the same temperature to give the reaction mass having 2,N-dimethyl-2-(trimethylsilyIoxy)-N-(3,3-diphenylpropyl)- 1-propanamine.
  • 14
  • C20H25N2O8PS [ No CAS ]
  • [ 100442-33-9 ]
  • [ 132866-11-6 ]
YieldReaction ConditionsOperation in experiment
Example 2: Preparation of crude l,4-dihvdro-2,6-dimethyl-4-(3- nitrophenyl)-3 ,5 -pyridinedicarboxylic acid [2-|Y3,3- diphenylpropyl)methylamino]-l,l-dimethylethyl1 methyl ester hydrochloride (crude lercanidipine hydrochloride)2.31 mL of triethylamine and 3.1 g of diethylchlorothiophosphate were added to 5.0 g of 2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-l,4- dihydropyridine-3-carboxylic acid (2) in 50 mL of toluene. The mixture was stirred at room temperature for one hour. After formation of a substituted phosphonoester derivative (5) as an intermediate was confirmed by thin layer chromatography (TLC), 4.49 g of 2, N-dimethyl-N-(3,3-diphenylpropyl)-l-amino- 2-propanol (3) was added thereto. The resulting mixture was refluxed for 4 hours. The reaction mixture was treated with activated carbon and was then concentrated under reduced pressure to remove toluene therefrom. The residue was dissolved in 30 mL of ethyl acetate. The organic phase was washed sequentially with 11 mL of a 10% NaOH aqueous solution, 11 mL of distilled water, 13.1 mL of 6N HCl and 11 mL of distilled water. An organic layer was separated, dried with activated carbon and anhydrous sodium sulfate for 30 min and concentrated under reduced pressure. The residue was dissolved in 15.7 mL of tetrahydrofuran and was then seeded with 50 mL of lercanidipine hydrochloride. The lercanidipine hydrochloride (dispersion) was stirred at 20 to 25 C for 24 hours, filtered and dried under vacuum to obtain 8.1 g of crude <n="10"/>lercanidipine hydrochloride (theoretical yield: 83.1%).IH NMR (DMSO-d6, 400MHz)(ppm): 10. 8 ~9.4 (bb, IH), 9.5 (bs, IH), 8.30- 8.05 (m, 2H), 7.85 ~ 7.60 (m, 2H), 7.55 ~ 7.20 (m, 10H), 5.05 (s, IH), 4.15 -3.35 (m, 6H), 3.20 -2.15 (m, 13H), 2.6 (s, 3H), 1.50 (s, 6H).
  • 15
  • C20H25N2O9P [ No CAS ]
  • [ 100442-33-9 ]
  • [ 132866-11-6 ]
YieldReaction ConditionsOperation in experiment
Example 1: Preparation of crude l,4-dihvdro-2,6-dimethyl-4-(3- nitrophenyl)-3 ,5 -pyridinedicarboxylic acid [2-|Y3,3- diphenylpropyl)methylamino~|- 1,1 -dimethyl ethyl] methyl ester hydrochloride (crude lercanidipine hydrochloride)2.31 mL of triethylamine and 2.4 mL of diethylchlorophosphate were added to 5.0 g of 2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-l,4- dihydropyridine-3-carboxylic acid (2) in 50 mL of toluene. The mixture was stirred at room temperature for one hour. After formation of a substituted phosphonoester derivative (5) as an intermediate was confirmed by thin layer chromatography (TLC), 4.49 g of 2, N-dimethyl-N-(3,3-diphenylpropyl)-l-amino-2-propanol (3) was added thereto (5). The resulting mixture was refluxed for 4 hours. The reaction mixture was treated with activated carbon and was then <n="9"/>concentrated under reduced pressure to remove toluene therefrom. The residue was dissolved in 30 mL of ethyl acetate. The organic phase was washed sequentially with 11 mL of a 10% NaOH aqueous solution, 11 mL of distilled water, 13.1 mL of 6N HCl and 11 mL of distilled water. An organic layer was separated, dried with activated carbon and anhydrous sodium sulfate for 30 min and concentrated under reduced pressure. The residue was dissolved in 15.7 mL of tetrahydrofuran and was then seeded with 50 mL of lercanidipine hydrochloride. The lercanidipine hydrochloride (dispersion) was stirred at 20 to 25 C for 24 hours, filtered and dried under vacuum to obtain 8.3 g of crude lercanidipine hydrochloride (theoretical yield: 85.1%).IH NMR (DMSO-d, 400MHz) (ppm): 10. 8 -9.4 (bb, IH), 9.5 (bs, IH), 8.30 - 8.05 (m, 2H), 7.85 -7.60 (m, 2H), 7.55 -7.20 (m, 10H), 5.05 (s, IH), 4.15 - 3.35 (m, 6H), 3.20 -2.15 (m, 13H), 2.6 (s, 3H), 1.50 (s, 6H).
  • 16
  • [ 105-45-3 ]
  • [ 100442-33-9 ]
  • [ 100427-51-8 ]
YieldReaction ConditionsOperation in experiment
zinc; In xylene; at 25 - 145℃; for 7.0h; 2,N-Dimethyl-N-(3,3-diphenylpropyl)-l-amino-2-propanol (5g) and methyl acetoactate (7.5g) were dissolved in xylene (50 ml) at 25-30C followed by the addition of zinc dust (1.75g). The reaction mixture was heated at 140-145C for 7 hours. Next,25 xylene was distilled out along with simultaneous addition of xylene in order to maintain the volume of xylene in the reaction mixture. The reaction mixture was cooled at 25- 30C followed by filtration to remove the catalyst. Distillation was carried out to remove xylene under reduced pressure. The resulting residue was degassed for 1 hour to produce title compound as viscous brown oil.
  • 17
  • [ 100442-33-9 ]
  • [ 132866-11-6 ]
 

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