Hydrogen Bromide → 3-(3-Hydroxyphenyl)-1-propyl-2-piperidone

HRID 1463117Notes

Reaction equation

HRID 1463117 reaction equation
Br[C:2]1[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=1[CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH3:17])[C:10]1=[O:18].Br>ClCCl.C(O)(=O)C>[OH:8][C:7]1[CH:2]=[C:3]([CH:9]2[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH3:17])[C:10]2=[O:18])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 130707403-(2-Bromo-3-oxocyclohex-1-enyl)-1-propyl-2-piperidone

Product 1

HCID 130707413-(3-Hydroxyphenyl)-1-propyl-2-piperidoneYield 87.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

The product of Example 8 (10.5 g, 33.4 mM) in dichloromethane (70 ml) was treated with 48% hydrogen bromide in acetic acid (ca 0.5 ml). After 16 h the solvent was evaporated under reduced pressure and the residue was partitioned between chloroform and water. The organic phase was dried and evaporated and the residue was chromatographed on alumina (neutral, grade 3) using 4% methanol in chloroform as eluant. The appropriate fractions were avaporated and recrystallised from ether to yield the title compound (6.8 g) m.p. 61°-3° (Found: C, 71.9; H, 7.8; 5.6% C14H19NO2 requires C, 72.1; H, 8.2; 6.0%).

Workup

  1. customAfter 16 h the solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between chloroform and water
  3. customThe organic phase was dried
  4. customevaporated
  5. customthe residue was chromatographed on alumina (neutral, grade 3)
  6. customrecrystallised from ether

Sources & evidence

ORD record
ord-88fe0ce07a3d42e0b292a4673d71ffe6
Source dataset
uspto-grants-1984_07
Patent number
US04463177

Reaction notes

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