N-Methylbenzeneethanamine → HCID 10646909, compound

HRID 2253736Notes

Reaction equation

HRID 2253736 reaction equation
[C:1](/[CH:5]=[CH:6]\[C:7]1[CH:8]=[C:9]([CH2:21][C:22]([OH:24])=O)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([O:3][CH3:4])=[O:2].[CH3:25][NH:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[CH3:25][N:26]([CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:22](=[O:24])[CH2:21][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:7](/[CH:6]=[CH:5]\[C:1]([O:3][CH3:4])=[O:2])[CH:8]=1

Participants

4

Reactant 2

HCID 11503N-MethylbenzeneethanamineHCID 10687571HCID 10687571, compound

Product 1

HCID 10646909HCID 10646909, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.85 g (5.69 mmoles) of cis-3-carbomethoxyvinyl-4-benzyloxyphenylacetic acid in 50 ml of CH2Cl2 is added 1.02 g (6.26 mmoles) if 1,1'-carbonyldiimadazole. After 15 minutes, 827 ml (5.69 mmoles) of N-methyl-N-phenethylamine is added. After 5 hours, the reaction mixture is concentrated in vacuo and is purified flash chromatography to yield cis-N-methyl-N-phenethyl-2-[4-benzyloxy-3-(2-carbomethoxyvinyl)phenyl]acetamide which is used directly in the next step.

Workup

  1. waitAfter 5 hours
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. customis purified flash chromatography

Sources & evidence

ORD record
ord-7261d1db392a4d40b04ab0d40a4c5212
Source dataset
uspto-grants-1993_08
Patent number
US05232948

Reaction notes

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