Sodium Carbonate → 4-(4-Fluorobenzoyl)-1-piperidinebutanenitrile

HRID 978439Notes

Reaction equation

HRID 978439 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]#[N:6].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[O:15])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CC(=O)C>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:2][CH2:3][CH2:4][C:5]#[N:6])[CH2:18][CH2:17]2)=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123364-ChlorobutyronitrileHCID 27244404-(4-Fluorobenzoyl)piperidine

Product 1

HCID 138512004-(4-Fluorobenzoyl)-1-piperidinebutanenitrile

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5 parts of 4-chlorobutanenitrile, 10 parts of (4-fluorophenyl)(4-piperidinyl)methanone, 10 parts of sodium carbonate and 200 parts of 4-methyl-2-pentanone was stirred and refluxed overnight. The reaction mixture was filtered and the filtrate was evaporated. The oily residue was crystallized from 2,2'-oxybispropane. The product was filtered off and recrystallized from 2,2'-oxybispropane, yielding 6.1 parts of 4-(4-fluorobenzoyl)-1-piperidinebutanenitrile; mp. 100° C. (5).

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe oily residue was crystallized from 2,2'-oxybispropane
  5. filtrationThe product was filtered off
  6. customrecrystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-743b1915a9fb425b8f87908e2974f07a
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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