Water → HCID 15680083, compound

HRID 373874Notes

Reaction equation

HRID 373874 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23]C(=O)C)=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[K+].O>CO>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([CH:15]([CH:12]2[CH2:13][CH2:14][N:9]([CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:10][CH2:11]2)[OH:16])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4192641Potassium borohydrideHCID 15680075HCID 15680075, compound

Product 1

HCID 15680083HCID 15680083, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To N-[4-[[1-(2-phenylethyl)-4-piperidinyl]carbonyl]phenyl]acetamide (40.0 g, 114 mmol) in methanol (900 ml) was added potassium borohydride (16 g, 300 mmol), in small portions, over a 6 hour period. Water (200 ml) was added and the solution was stirred for 20 hours. The solution was concentrated and partitioned between water and dichloromethane. The layers were separated, the organic layer dried (MgSO4), filtered, and concentrated. The resulting material was chromatographed on silica gel, eluting with 10% methanol in chloroform. The appropriate fractions were combined, evaporated, and the resulting solid recrystallized from 2-propranol/water to afford α-(4-aminophenyl)-1-(2-phenylethyl)-4-piperidine methanol as a white solid (7.5 g, 21%): m.p. 129°-130° C.

Workup

  1. concentrationThe solution was concentrated
  2. custompartitioned between water and dichloromethane
  3. customThe layers were separated
  4. dry with materialthe organic layer dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting material was chromatographed on silica gel
  8. washeluting with 10% methanol in chloroform
  9. customevaporated
  10. customthe resulting solid recrystallized from 2-propranol/water

Sources & evidence

ORD record
ord-f67896bf73c9469fbd55fa3379c550ac
Source dataset
uspto-grants-1992_11
Patent number
US05166211

Reaction notes

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