Triphenylphosphine → 4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(3-methoxy-butoxy)-benzamide

HRID 620284

반응식

HRID 620284 반응식
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([OH:19])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:39][O:40][CH:41]([CH3:45])[CH2:42][CH2:43]O.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[O:7])=[C:4]([O:19][CH2:43][CH2:42][CH:41]([O:40][CH3:39])[CH3:45])[CH:3]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 172913-Methoxy-1-butanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9817332o-Desmethyl metoclopramide

생성물 1

HCID 99293764-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(3-methoxy-butoxy)-benzamide수율 52.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A stirred solution of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (1.715 g, 6 mmoles; prepared according to Preparation 1B), triphenylphosphine (1.58 g, 6 mmoles), 3-methoxy-1-butanol (0.62 g, 6 mmoles) in dry tetrahydrofuran (50 ml) was treated dropwise with diethyl azodicarboxylate (1.1 g of 95% purity material, 6 mmoles). The solution was left to stir overnight. After evaporation of the solvent the residue was dissolved in methylene chloride. The solution was washed with 0.4N NaOH, water, dried and the solvent evaporated. The residue was chromatographed over deactivated silica using methylene chloride (100), methanol (2.5), ammonium hydroxide (0.5) solvent system. The appropriate fractions were combined and the solvent evaporated. The residue (1.7 g) was crystallized from toluene to yield 1.17 g (52%) of the title compound, m.p. 76°-78° C.

후처리

  1. waitThe solution was left
  2. customAfter evaporation of the solvent the residue
  3. dissolutionwas dissolved in methylene chloride
  4. washThe solution was washed with 0.4N NaOH, water
  5. customdried
  6. customthe solvent evaporated
  7. customThe residue was chromatographed over deactivated silica
  8. customthe solvent evaporated
  9. customThe residue (1.7 g) was crystallized from toluene

출처 및 근거

ORD 기록
ord-56c9973285944906806d04864c153888
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04820715

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