Triethylamine → HCID 19829407, compound

HRID 1493869Notes

Reaction equation

HRID 1493869 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([Cl:29])=[O:28])=[CH:25][CH:24]=1.C(N(CC)CC)C>ClC(Cl)Cl>[ClH:29].[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[C:27](=[O:28])[C:26]2[CH:30]=[CH:31][C:23]([F:22])=[CH:24][CH:25]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 5109634Despropionyl N-benzyl p-fluoro norfentanyl

Product 1

HCID 19829407HCID 19829407, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-Benzyl-4-(4-fluoroanilino)piperidine (2.8 g), dissolved in trichloromethane (30 cc), is stirred for 18 hours with 4-fluorobenzoic acid chloride (2 cc) and in the presence of triethylamine (5 cc). The reaction mixture is then washed twice with sodium hydroxide solution (3N) (30 cc) thereafter with water (30 cc). The organic phase is then dried over magnesium sulphate and thereafter concentrated under reduced pressure (5.2 kPa). By the addition of a 3.4N solution (5 cc) of hydrochloric acid in isopropanol and recrystallization in acetone/ethanol mixture (50:50 by volume) (100 cc), N-(1-benzyl-4-piperidyl)-N-(4-fluorophenyl)-4-fluorobenzamide hydrochloride (3.2 g) is obtained in the form of a white powder, m.p. 210° C.

Workup

  1. washThe reaction mixture is then washed twice with sodium hydroxide solution (3N) (30 cc)
  2. dry with materialThe organic phase is then dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure (5.2 kPa)
  4. additionBy the addition of a 3.4N solution (5 cc) of hydrochloric acid in isopropanol and recrystallization in acetone/ethanol mixture (50:50 by volume) (100 cc)

Sources & evidence

ORD record
ord-8ec7717ca8d84c4db68070071b927c4f
Source dataset
uspto-grants-1991_06
Patent number
US05025013

Reaction notes

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