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

HRID 1179170Notes

Reaction equation

HRID 1179170 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-eff3ef32945148dda6ca57c14176a5f5
Source dataset
uspto-grants-2007_10
Patent number
US07279472B2

Reaction notes

Loading…