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

HRID 620284

Reaction equation

HRID 620284 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-56c9973285944906806d04864c153888
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Linked notes

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