1,3-Butanediol → HCID 14116936, compound

HRID 620285Notes

Reaction equation

HRID 620285 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.[CH2:39](O)[CH2:40][CH:41]([OH:43])[CH3:42].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][CH2:39][CH2:40][CH:41]([OH:43])[CH3:42])[CH:3]=1

Participants

6

Reactant 4

HCID 78961,3-ButanediolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9817332o-Desmethyl metoclopramide

Product 1

HCID 14116936HCID 14116936, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (2.86 g, 10 mmoles; prepared according to Preparation B), triphenylphosphine (2.62 g, 10 mmoles), (±) 1,3 butandiol (0.90 g, 10 mmoles) in dry tetrahydrofuran (50 ml) was treated dropwise with diethyl azodicarboxylate (1.75 g of 95% purity material, 10 mmoles). The solution was left to stir overnight. After evaporation of the solvent the residue was taken up 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 (3), ammonium hydroxide (0.5) solvent system. The appropriate fractions were combined and the solvent evaporated. The residue was crystallized from methylene chloride-pentane to yield 1.05 g (29%) of the title compound. m.p. 136.5°-137.5° C. An additional amount of 0.56 g of material was obtained from the mother liquor after crystallization from toluene, followed by recrystallization from methylene chloride-pentate, and from a dilute solution of ethyl acetate, m.p. 135°-137° C.

Workup

  1. waitThe solution was left
  2. customAfter evaporation of the solvent the residue
  3. washThe solution was washed with 0.4N NaOH, water
  4. customdried
  5. customthe solvent evaporated
  6. customThe residue was chromatographed over deactivated silica
  7. customthe solvent evaporated
  8. customThe residue was crystallized from methylene chloride-pentane

Sources & evidence

ORD record
ord-13db78cc21184296b148a5d4f8b2bd21
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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