Benzylamine → Hydrocinnamamide, N-benzyl-p-methoxy-

HRID 1975280Notes

Reaction equation

HRID 1975280 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1.C(N(CC)CC)C.ClC(OCC)=O.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[CH2:27]([NH:34][C:11](=[O:13])[CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 957503-(p-Methoxyphenyl)propionic acid

Product 1

HCID 64876Hydrocinnamamide, N-benzyl-p-methoxy-Yield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10.80 g (0.060 mole) of 3-(4-methoxyphenyl) propanoic acid and 6.57 g (0.065 mole of triethylamine in 25 ml dichloromethane at about 0.5° C., 6.84 g (0.063 mole) of ethyl chloroformate was added dropwise. The mixture was stirred for about 15 minutes at a temperature of about 5° to 10° C., then 6.96 g (0.065 mole) of benzylamine were added. The resulting mixture was stirred for about thirty minutes, and the solvent was evaporated. The residue was slurried in 5% aqueous sodium hydroxide. The solid was collected by filtration and rinsed with water until neutral. The washing process was repeated using 5% hydrochloric acid. The residue was dried under vacuum to give 11.0 g of the above-identified product, melting point 92°-94° C., which was suitable for use in step (b).

Workup

  1. stirringThe resulting mixture was stirred for about thirty minutes
  2. customthe solvent was evaporated
  3. filtrationThe solid was collected by filtration
  4. washrinsed with water until neutral
  5. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-ae4e9d99359b47f28933946837c2a7f1
Source dataset
uspto-grants-1994_02
Patent number
US05286252

Reaction notes

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