Methyl Isobutyl Ketone → HCID 20278954, compound

HRID 1248207Notes

Reaction equation

HRID 1248207 reaction equation
Cl[CH2:2][CH2:3][CH:4]([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7].Cl.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[CH2:6]([O:5][CH:4]([O:8][CH2:9][CH3:10])[CH2:3][CH2:2][N:24]1[CH2:25][CH2:26][CH:21]([C:19]([C:16]2[CH:15]=[CH:14][C:13]([F:12])=[CH:18][CH:17]=2)=[O:20])[CH2:22][CH2:23]1)[CH3:7]

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 962173-Chloro-1,1-diethoxypropaneHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochloride

Product 1

HCID 20278954HCID 20278954, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.5 parts of 1-chloro-3,3-diethoxypropane, 12.15 parts of (4-fluorophenyl)(4-piperidinyl)methanone hydrochloride, 10.6 parts of sodium carbonate and 120 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. The reaction mixture is cooled, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of methylbenzene and 2,2'-oxybispropane, yielding 9 parts (53%) of [1-(3,3-diethoxypropyl)-4-piperidinyl](4-fluorophenyl)methanone.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe residue is crystallized from a mixture of methylbenzene and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-eb18df59575a4e47ad0deef2e4e37287
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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