Benzylamine → Ethyl 3-(benzylamino)-3-methylbutanoate

HRID 561118Notes

Reaction equation

HRID 561118 reaction equation
[CH3:1][C:2]([CH3:9])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCO>[CH2:10]([NH:17][C:2]([CH3:9])([CH3:1])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 12516Ethyl 3,3-dimethylacrylate

Product 1

HCID 288946Ethyl 3-(benzylamino)-3-methylbutanoateYield 21.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3,3-dimethylacrylate (19.3 g, 0.151 mol) in EtOH (150 mL) was added benzylamine (16.2 g, 0.151 mol) and refluxed for 24 h. The reaction mixture was concentrated in vacuo. The distillation of the residue gave ethyl 3-benzylamino-3-methylbutyrate as a colorless oil (7.48 g, 21%).

Workup

  1. temperaturerefluxed for 24 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. distillationThe distillation of the residue

Sources & evidence

ORD record
ord-319b932dd8ae4c888979a6e751abcd91
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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