N-Methylbenzylamine → 3-(Benzyl-methyl-amino)-butyric acid methyl ester

HRID 353947Notes

Reaction equation

HRID 353947 reaction equation
[CH2:1]([NH:8][CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([O:15][CH3:16])(=[O:14])/[CH:11]=[CH:12]/[CH3:13]>>[CH3:16][O:15][C:10](=[O:14])[CH2:11][CH:12]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:9])[CH3:13]

Participants

3

Reactant 2

HCID 7669N-MethylbenzylamineHCID 638132Methyl Crotonate

Product 1

HCID 232160883-(Benzyl-methyl-amino)-butyric acid methyl esterYield 110.4%

Procedure

Benzyl-methyl-amine (20 g, 165 mmol, 1.0 equiv) was added neat to methyl crotonate (19.8 g, 198 mmol, 1.2 equiv). The resulting solution was stirred at room temperature for 72 h. The excess crotonic ester was removed in vacuo to yield the desired product (40.3 g,˜100%) which was used without further purification; MS, m/z 222=M+1.

Workup

  1. customThe excess crotonic ester was removed in vacuo

Sources & evidence

ORD record
ord-70856cd33476409c83979d71fcefaf77
Source dataset
uspto-grants-2004_06
Patent number
US06756372B2

Reaction notes

Loading…