N-Methylbenzylamine → HCID 10976320, compound

HRID 1925771Notes

Reaction equation

HRID 1925771 reaction equation
Cl.[CH3:2][CH:3](NCCC(O)=O)[CH2:4][CH2:5][CH2:6]C.[CH3:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.BrCCCCC.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:14][N:15]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 7669N-MethylbenzylamineHCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 86645229HCID 86645229, compound

Product 1

HCID 10976320HCID 10976320, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The present invention provides an alternate process for the synthesis of 3-[N-(methylpentyl)amino]propionic acid (III) wherein N-methyl benzyl amine is condensed with 1-bromo pentane in presence of potassium carbonate, using acetone as solvent to give N-methyl N-pentyl benzyl amine. This is debenzylated using palladium on carbon as catalyst and alcohol as solvent. The resulting product N-methyl pentyl amine is condensed with methyl acrylate in toluene to get 3-[N-(methylpentyl)amino]propionate, which is further hydrolysed to obtain Intermediate III.

Workup

  1. customThe present invention provides an alternate process

Sources & evidence

ORD record
ord-ca97add7c0924b36a4e84c798bc19062
Source dataset
uspto-grants-2012_05
Patent number
US08178712B2

Reaction notes

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