Hydrogen Bromide → HCID 13604908, compound

HRID 1981540Notes

Reaction equation

HRID 1981540 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([O:23]C)[CH:17]=3)[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br>C(O)(=O)C>[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([OH:23])[CH:17]=3)[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 20227416HCID 20227416, compound

Product 1

HCID 13604908HCID 13604908, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The 1-(3-phenylpropyl)-3-(4-fluoro-3-methoxyphenyl)-piperidine from Preparation 5 was reacted with 48% aqueous hydrobromic acid in glacial acetic acid using the procedure of Example 3. The product was chromatographed on silica gel, eluting with ethyl acetate/hexane/triethylamine (5:5:3). This afforded a 32% yield of the title compound, [alpha]D25 =-21.2° (c=1; C2H5OH).

Workup

  1. customThe product was chromatographed on silica gel
  2. washeluting with ethyl acetate/hexane/triethylamine (5:5:3)

Sources & evidence

ORD record
ord-df953294b56748c0832b1af677e43df3
Source dataset
uspto-grants-1986_06
Patent number
US04593037

Reaction notes

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