4-(4-Fluorobenzoyl)piperidine → HCID 14392397, compound

HRID 1193992Notes

Reaction equation

HRID 1193992 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][CH2:4][N:5]1[C:14](=[O:15])[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH:8]2[C:6]1=[O:7].[F:17][C:18]1[CH:31]=[CH:30][C:21]([C:22]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[O:23])=[CH:20][CH:19]=1>C(O)CCC>[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([CH:24]2[CH2:29][CH2:28][N:27]([CH2:16][CH:2]([OH:1])[CH2:3][CH2:4][N:5]3[C:14](=[O:15])[CH:9]4[CH2:10][CH2:11][CH2:12][CH2:13][CH:8]4[C:6]3=[O:7])[CH2:26][CH2:25]2)=[O:23])=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 27244404-(4-Fluorobenzoyl)piperidineHCID 144414952-[2-(Oxiran-2-yl)ethyl]hexahydro-1H-isoindole-1,3(2H)-dione

Product 1

HCID 14392397HCID 14392397, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of N-(3,4-epoxybutyl)cyclohexane-1,2-dicarboximide (3 g), 4-(4-fluorobenzoyl)piperidine (3.23 g) and n-butanol (62 ml) was refluxed for 6 hours, followed by evaporation of n-butanol under reduced pressure. The residue was purified by silica gel column chromatography to give the objective compound (2.3 g). Yield, 38.2%. M.P., 121°-122° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customfollowed by evaporation of n-butanol under reduced pressure
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5d3595093edf4c0085676d00ea179a65
Source dataset
uspto-grants-1989_03
Patent number
US04812461

Reaction notes

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