Sodium borohydride → 4-Piperidinemethanol, 4-(phenylamino)-1-(2-phenylethyl)-

HRID 37369Notes

Reaction equation

HRID 37369 reaction equation
[BH4-].[Na+].[C:3]1([NH:9][C:10]2([CH:24]=[O:25])[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO.O>[C:3]1([NH:9][C:10]2([CH2:24][OH:25])[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 199356594-(N-phenylamino)-1-(2-phenylethyl)piperidine-4-carboxaldehyde

Product 1

HCID 122982044-Piperidinemethanol, 4-(phenylamino)-1-(2-phenylethyl)-Yield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (2 g) was added portionwise to a stirred solution of 4-(N-phenylamino)-1-(2-phenylethyl)piperidine-4-carboxaldehyde (2 g) in methanol (2 g) at room temperature for 2 hours. The mixture was diluted with water, extracted with chloroform and the combined extracts washed, dried over MgSO4 and concentrated. The residue was chromatographed on silica gel, using chloroform-methanol 19:1 as eluant, to afford 4-(N-phenylamino)-1-(2-phenylethyl)-4-piperidinylmethanol (1.65 g), m.p. 98°-99° C.

Workup

  1. extractionextracted with chloroform
  2. washthe combined extracts washed
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-35de2818d95847eebb2eea74c0f03d1e
Source dataset
uspto-grants-1995_05
Patent number
US05420280

Reaction notes

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