Potassium Carbonate → 1-(4-Benzenesulfonyl-4-methylpentyl)-3-hydroxypiperidine

HRID 2212093Notes

Reaction equation

HRID 2212093 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([CH3:16])([S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH3:6].[OH:17][CH:18]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:10]1([S:7]([C:5]([CH3:16])([CH3:6])[CH2:4][CH2:3][CH2:2][N:20]2[CH2:21][CH2:22][CH2:23][CH:18]([OH:17])[CH2:19]2)(=[O:9])=[O:8])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 232933-HydroxypiperidineHCID 69663286(5-Bromo-2-methylpentane-2-sulfonyl)benzene

Product 1

HCID 696627361-(4-Benzenesulfonyl-4-methylpentyl)-3-hydroxypiperidineYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(5-Bromo-2-methylpentane-2-sulfonyl)benzene (5 g, 16.4 mmol), 3-hydroxypiperidine (2 g, 20 mmol) and potassium carbonate (4.5 g, 33 mmol) in acetonitrile (50 ml) were stirred at 50° C. for 18 hours. The cooled reaction mixture was partitioned between ethyl acetate and brine. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 120:8:1 dichloromethane/methanol/ammonia, to give the title compound (5.2 g, 98%).

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned between ethyl acetate and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with 120:8:1 dichloromethane/methanol/ammonia

Sources & evidence

ORD record
ord-3a47ce98f18e48ccab80ffa968dac6fd
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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