Methyl Isobutyl Ketone → HCID 20278956, compound

HRID 1156331Notes

Reaction equation

HRID 1156331 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14].Cl.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([CH:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:16])[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N+:13]([O-:15])=[O:14])[CH2:29][CH2:28]2)=[O:26])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 20085691N-(3-Bromopropyl)-2-nitrobenzamide

Product 1

HCID 20278956HCID 20278956, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 14.4 parts of N-(3-bromopropyl)-2-nitrobenzamide, 12.2 parts of (4-fluorophenyl) (4-piperidinyl)methanone hydrochloride, 16 parts of sodium carbonate and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 3 hours using a water-separator. The reaction mixture is cooled, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 18 parts (87%) of N-[3-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl]-2-nitrobenzamide as an oily residue.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated

Sources & evidence

ORD record
ord-b9115d543f7744d2afed4f3905c46eae
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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