Triethylamine → 4-(4-Fluorobenzoyl)-1-(4-nitrobenzoyl)piperidine

HRID 648507Notes

Reaction equation

HRID 648507 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[F:14][C:15]1[CH:28]=[CH:27][C:18]([C:19]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:20])=[CH:17][CH:16]=1.C(N(CC)CC)C>C(Cl)Cl>[F:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([CH:21]2[CH2:26][CH2:25][N:24]([C:8](=[O:9])[C:7]3[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:23][CH2:22]2)=[O:20])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochloride

Product 1

HCID 136039654-(4-Fluorobenzoyl)-1-(4-nitrobenzoyl)piperidineYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrobenzoyl chloride (3.08 g) was added slowly to a stirred mixture of 4-(4-fluorobenzoyl)piperidine hydrochloride (4.0 g) and triethylamine (4.98 g) in methylene chloride (110 ml) at room temperature. The resulting mixture was stirred at this temperature for 1 hour, washed with 1N hydrochloric acid, saturated sodium bicarbonate solution, and brine, dried over magnesiun sulfate and concentrated in vacuo. The residue was recrystallized from a mixture of acetone and methanol to give 4-(4-fluorobenzoyl)-1-(4-nitrobenzoyl)piperidine (5.0 g) as colourless crystals.

Workup

  1. washwashed with 1N hydrochloric acid, saturated sodium bicarbonate solution, and brine
  2. dry with materialdried over magnesiun sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from a mixture of acetone and methanol

Sources & evidence

ORD record
ord-62f909a151c64ea7bb61e29664fb3cbd
Source dataset
uspto-grants-1988_04
Patent number
US04735952

Reaction notes

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