1-Benzyl-4-piperidone → 1'-Benzyl-6-bromospiro[chroman-2,4'-piperidin]-4-one

HRID 2046697Notes

Reaction equation

HRID 2046697 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].[CH2:12]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1CCCC1>CO>[CH2:12]([N:19]1[CH2:24][CH2:23][C:22]2([CH2:1][C:2](=[O:3])[C:4]3[C:5](=[CH:6][CH:7]=[C:8]([Br:10])[CH:9]=3)[O:11]2)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 128879551'-Benzyl-6-bromospiro[chroman-2,4'-piperidin]-4-oneYield 66.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-hydroxy-5-bromoacetophenone (5.85 g, 27.2 mmol), N-benzyl-4-piperidone (5.14 g, 27.21 mmol) and pyrrolidine (1.11 ml, 13.60 mmol) in MeOH (100 ml) was heated to reflux. After 11 h, the solvent was removed under vacuum and the crude mixture was purified by column chromatography (eluent: hexane/AcOEt 90:10 to 70:30) to give 1′-benzyl-6-bromo-spiro[chromane-2,4′-piperidine]-4-one (7.0 g) as a yellow solid.

Workup

  1. temperaturewas heated to reflux
  2. customthe solvent was removed under vacuum
  3. customthe crude mixture was purified by column chromatography (eluent: hexane/AcOEt 90:10 to 70:30)

Sources & evidence

ORD record
ord-17ca978b009146688b0f96a23a9532da
Source dataset
uspto-grants-2013_11
Patent number
US08592444B2

Reaction notes

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