Benzylamine → Diethyl 3-benzylamino-2-pentenedioate

HRID 893888

Reaction equation

HRID 893888 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][CH2:10][O:11][C:12]([CH2:14][C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=O)=[O:13]>C1(C)C=CC=CC=1>[CH2:10]([O:11][C:12](=[O:13])[CH:14]=[C:15]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:9]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 66045Diethyl acetonedicarboxylate

Product 1

HCID 70353029Diethyl 3-benzylamino-2-pentenedioate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Benzylamine (89.1 g, 0.83 moles) is added over 10 minutes to a suspension of 5 A powdered molecular sieves (270 g) and diethyl 1,3-acetonedicarboxylate (160 g) (0.79 moles) in 350 ml toluene (external cooling applied to control exotherm). The suspension is stirred at room temperature for 14-17 hours and then filtered to provide 2. The filter cake is washed with three portions of toluene. The combined filtrates may be used as is in the subsequent ketene reaction.

Workup

  1. filtrationfiltered
  2. customto provide 2
  3. washThe filter cake is washed with three portions of toluene
  4. customas is in the subsequent ketene reaction

Sources & evidence

ORD record
ord-514f8daa25ec4e1292d3fd4e86d862e5
Source dataset
uspto-grants-1981_08
Patent number
US04282148

Linked notes

Loading…