Benzylamine → Diethyl 3-benzylamino-2-pentenedioate

HRID 1262955Notes

Reaction equation

HRID 1262955 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 5A 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 in the subsequent ketene reaction.

Workup

  1. filtrationfiltered
  2. customto provide 2
  3. washThe filter cake is washed with three portions of toluene
  4. customThe combined filtrates may be used as in the subsequent ketene reaction

Sources & evidence

ORD record
ord-3d56d55105f14d65bb30d9b980cfad2f
Source dataset
uspto-grants-1984_06
Patent number
US04454332

Reaction notes

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