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

HRID 915221Notes

Reaction equation

HRID 915221 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-17befd3828d64850a9f6ab6486caac59
Source dataset
uspto-grants-2007_09
Patent number
US07265132B2

Reaction notes

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