O-Methyltyramine → N-[2-(4-methoxyphenyl)ethy]-1-phenylcyclobutane carboxamide

HRID 440528Notes

Reaction equation

HRID 440528 reaction equation
[C:1]1([C:7]2([C:11](Cl)=[O:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([CH2:20][CH2:21][NH2:22])=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl>[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([CH2:20][CH2:21][NH:22][C:11]([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:10][CH2:9][CH2:8]2)=[O:12])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 4657O-MethyltyramineHCID 8471TriethylamineHCID 232948921-Phenylcyclobutanecarbonyl chloride

Product 1

HCID 23192546N-[2-(4-methoxyphenyl)ethy]-1-phenylcyclobutane carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-phenylcyclobutanecarbonyl chloride (129 g) in dichloromethane (500 ml) was added under nitrogen over 1.5 hours to a stirred mixture of 4-methoxyphenethylamine (99.5 g), dichloromethane (500 ml) and triethylamine (110 ml). The mixture was stirred at 20°-25° C. for one hour and allowed to stand for 16 hours. The reaction mixture was washed with 2N hydrochloric acid, water and 2N aqueous sodium hydroxide solution, dried and evaporated to give N-[2-(4-methoxyphenyl)ethy]-1-phenylcyclobutane carboxamide.

Workup

  1. waitto stand for 16 hours
  2. washThe reaction mixture was washed with 2N hydrochloric acid, water and 2N aqueous sodium hydroxide solution
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-ad5cf33f3c44468284c25f5fe864081e
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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