Sodium borohydride → alpha-(6-Chloro-2-naphthyl)-4-piperidinemethanol

HRID 1389864Notes

Reaction equation

HRID 1389864 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:20])[CH:16]=3)[CH:11]=2)=[O:9])[CH2:4][CH2:3]1.[BH4-].[Na+]>C(O)C>[Cl:20][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([CH:8]([CH:5]1[CH2:6][CH2:7][NH:2][CH2:3][CH2:4]1)[OH:9])[CH:19]=[CH:18]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 705701616-Chloro-2-naphthyl 4-piperidyl ketone hydrochloride

Product 1

HCID 20295598alpha-(6-Chloro-2-naphthyl)-4-piperidinemethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.47 g (12.7 mmoles) of (6-chloro-2-naphthyl) 4-piperidyl ketone hydrochloride is suspended in 200 ml of absolute ethanol and 1.5 g (4 mmoles) of sodium borohydride added. The reaction mixture is stirred for 18 hours and concentrated in vacuo. The residue is triturated with water and aqueous sodium hydroxide added to produce a basic solution which is extracted with toluene/methylene chloride. The organic phase is washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to yield α-(6-chloro-2-naphthyl)-4-piperidinemethanol.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is triturated with water and aqueous sodium hydroxide
  3. additionadded
  4. customto produce a basic solution which
  5. extractionis extracted with toluene/methylene chloride
  6. washThe organic phase is washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba3d7726b1dc46aab8439fe4286fbbcf
Source dataset
uspto-grants-1981_01
Patent number
US04246268

Reaction notes

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