Sodium borohydride → HCID 23003650, compound

HRID 396314Notes

Reaction equation

HRID 396314 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH:12]([CH2:17][CH2:18][CH3:19])[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][CH2:18][CH3:19])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13016601HCID 13016601, compound

Product 1

HCID 23003650HCID 23003650, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.5 g, 15.6 mmole) was added to the stirred solution of 1-benzyl-3-n-propylpiperidin-4-one (4.0 g, 17.3 mmole) in methanol (25 ml) at 0-5° C. over a period of 5 min, and stirring was continued for 1 hr at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water (20 ml) and extracted with ethyl acetate. The ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to furnish 1-benzyl-4-hydroxy-3-n-propylpiperidine as oil. Yield 3.3 g (81%), C15H23NO, m/z 234 (M+l).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with water (20 ml)
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1554478d22304cdfbe9b5e889b39ca41
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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