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

HRID 1850873

반응식

HRID 1850873 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-bef0d4a902b649ad986996cdb96c4d6a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957089B2

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