Sodium borohydride → 1-Benzyl-3-ethyl-4-hydroxypiperidine

HRID 396304Notes

Reaction equation

HRID 396304 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH:12]([CH2:17][CH3:18])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH:12]([CH2:17][CH3:18])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 64909601-Benzyl-3-ethylpiperidin-4-one

Product 1

HCID 230037101-Benzyl-3-ethyl-4-hydroxypiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.456 g, 12.0 mmole) was added to the stirred solution of 1-benzyl-3-ethyl piperidin-4-one (5.4 g, 24.0 mmole) in methanol (25 ml) at 0-5° C. over a period of 15 min, and stirring was continued for 30 min at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water (25 ml) and extracted with ethyl acetate (2×100 ml). The extract was dried (sodium sulphate) and concentrated to dryness to furnish 1-benzyl-3-ethyl-4-hydroxypiperidine product as oil, which was used as such in the next step. Yield 5.2 g (96%), C14H21NO, m/z 220 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with water (25 ml)
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. dry with materialThe extract was dried (sodium sulphate)
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0f81e856b6d2401bb89591ea33087e70
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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