Hydrochloric Acid → Primaperone [INN:DCF]

HRID 1578387Notes

Reaction equation

HRID 1578387 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:18])[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.Cl>[O-2].[O-2].[Mn+4].C1C=CC=CC=1>[N:12]1([CH2:11][CH2:10][CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21559992HCID 21559992, compound

Product 1

HCID 14641Primaperone [INN:DCF]Yield 100.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 2 g of 1-(p-fluorophenyl)-4-piperidino-1-butanol liberated from the hydrochloride, 20 ml of benzene, and 4 g of a fine powder of manganese dioxide was stirred for 8 hours at room temperature. After filtration, the precipitate was washed with 20 ml of benzene. The benzene washings and filtrate were combined and concentrated under reduced pressure to obtain oily γ-piperidino-p-fluorobutyrophenone (2 g in weight; infrared absorption spectrum, ν C=0 1678 cm-1). The said oily product was dissolved in 20 ml of ether, and gaseous hydrogen chloride was introduced therein to saturation. The precipitate formed was recrystallized from ethanol-ether to yield the hydrochloride melting at 180° - 181°C.

Workup

  1. filtrationAfter filtration
  2. washthe precipitate was washed with 20 ml of benzene
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-15cbc24504af4135b7087a758a4202f1
Source dataset
uspto-grants-1976_02
Patent number
US03936468

Reaction notes

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