O-Methyltyramine → 1-(4-chlorophenyl)-N-[2-(4-methoxyphenyl)ethyl]cyclopropanecarboxamide

HRID 1850873Notes

Reaction equation

HRID 1850873 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH2:24])=[CH:18][CH:17]=1.Cl.C(N=C=NCCCN(C)C)C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([NH:24][CH2:23][CH2:22][C:19]3[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=3)=[O:13])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4657O-MethyltyramineHCID 986061-(p-Chlorophenyl)cyclopropanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 604096681-(4-chlorophenyl)-N-[2-(4-methoxyphenyl)ethyl]cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-(4-chlorophenyl)cyclopropanecarboxylic acid (5.0 g, 25.3 mmol), 2-(4-methoxyphenyl)ethanamine (4.2 g, 28 mmol) and 4-N,N-Dimethylaminopyridin (3.3 g; 28 mmol) in methylenehloride (200 ml) was cooled to −10° C. N-ethyl-N′-(3-Dimethylaminopropyl)-carbodiimid hydrochloride (EDC, 5.3 g, 28 mmol) was added in several portions and the resulting mixture stirred overnight. The reaction mixture was poured into water and consecutively extracted with water, 2N NaOH and 1N HCl. Evaporation of the dried (NaSO4) extract yielded an oily residue that crystallized upon addition of n-heptan, which was used without further purification. Yield 7.0 g (21.2 mmol, 83%).

Workup

  1. extractionconsecutively extracted with water, 2N NaOH and 1N HCl
  2. customEvaporation of the
  3. dry with materialdried (NaSO4)
  4. extractionextract
  5. customyielded an oily residue that
  6. customcrystallized upon addition of n-heptan, which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-bef0d4a902b649ad986996cdb96c4d6a
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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