Sodium borohydride → 1-(2-Hydroxy-2-phenylethyl)-4-benzamidopiperidine

HRID 437226Notes

Reaction equation

HRID 437226 reaction equation
[BH4-].[Na+].[C:3]1([C:9](=[O:26])[CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13][CH2:12]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>[OH-].[Na+].CO>[OH:26][CH:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 214305611-Phenacyl-4-benzamidopiperidine

Product 1

HCID 214306391-(2-Hydroxy-2-phenylethyl)-4-benzamidopiperidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Sodium borohydride (6.00 g.) in 0.2N NaOH solution (60 ml.) was added dropwise to a stirred solution of 1-(2-phenyl-2-oxoethyl)-4-benzamidopiperidine (4.83 g.) in methanol (300 ml.). After refluxing the solution for 2 hours it was filtered and the filtrate concentrated to ca. 100 ml., whereupon the product crystallised out to give the title compound, m.p. 178°-180° C. (Found: C, 74.1; H, 7.5; N, 8.6. C20H24N2O2 requires C, 74.0; H, 7.5; N, 8.6%).

Workup

  1. temperatureAfter refluxing the solution for 2 hours it
  2. filtrationwas filtered
  3. concentrationthe filtrate concentrated to ca. 100 ml
  4. custom, whereupon the product crystallised out

Sources & evidence

ORD record
ord-7af9e24fefb04a678d86a86ecf30a513
Source dataset
uspto-grants-1977_06
Patent number
US04029801

Reaction notes

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