Hydrogen Bromide → (4-Fluorophenyl)(4-phenyl-4-piperidinyl)methanone hydrobromide hemihydrate

HRID 325920Notes

Reaction equation

HRID 325920 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13][CH2:12][N:11](C(OCC)=O)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[BrH:27]>O>[OH2:7].[BrH:27].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:25][CH:26]=1.[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:25][CH:26]=1.[BrH:27]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 13477817Ethyl 4-(4-fluorobenzoyl)-4-phenylpiperidine-1-carboxylate

Product 1

HCID 70478562(4-Fluorophenyl)(4-phenyl-4-piperidinyl)methanone hydrobromide hemihydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 14 parts of ethyl 4-(4-fluorobenzoyl)-4-phenyl-1-piperidinecarboxylate and 150 parts of a hydrobromic acid solution 48% in water was stirred and refluxed for 30 minutes. The reaction mixture was diluted with 100 parts of water and the whole was stirred while the mixture was allowed to cool to room temperature. The precipitated product was filtered off (filtrate I was set aside), washed with methylbenzene and stirred in 2-propanone. It was filtered off again (filtrate II was set aside) and dried, yielding a first fraction of 4.3 parts of (4-fluorophenyl) (4-phenyl-4-piperidinyl)methanone hydrobromide hemihydrate. Filtrates I and II were evaporated and the solid residue was stirred in 4-methyl-2-pentanone. The product was filtered off and dried, yielding a second fraction of 6.2 parts of (4-fluorophenyl) (4-phenyl-4-piperidinyl)methanone hydrobromide hemihydrate; mp. 173.4° C. Total yield: 73%. (intermediate 17).

Workup

  1. temperaturerefluxed for 30 minutes
  2. stirringthe whole was stirred while the mixture
  3. filtrationThe precipitated product was filtered off (filtrate I
  4. washwashed with methylbenzene
  5. stirringstirred in 2-propanone
  6. filtrationIt was filtered off again (filtrate II
  7. customdried

Sources & evidence

ORD record
ord-a681621a53354e9ab31d783a58168f35
Source dataset
uspto-grants-1984_04
Patent number
US04443451

Reaction notes

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