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

HRID 518152Notes

Reaction equation

HRID 518152 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-f5c9ccaf16f945b4968058080008a276
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

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