Water → HCID 21527762, compound

HRID 1658498Notes

Reaction equation

HRID 1658498 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]([OH:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]([C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6]1.[BH4-].[Na+].O.CCCCCC>C(O)C.CCOCC>[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]([OH:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]([CH:18]([OH:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6]1

Participants

7

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 4311764Sodium borohydrideHCID 12412621HCID 12412621, compound

Product 1

HCID 21527762HCID 21527762, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

10.0 Parts of 1-(2-dimethylaminoethyl)-3-benzoyl-4-hydroxy-4-phenylpiperidine is dissolved in 70 parts of ethanol. To this solution is slowly added 10.0 parts of sodium borohydride and the mixture heated to about 50°C. for 1/2 hour. After cooling to room temperature, the reaction mixture is poured into water. The resulting mixture is extracted three times with ethyl ether and the extracts are combined, dried over magnesium sulfate, and stripped of solvent under reduced pressure to give an oil. This oil is dissolved in ether and n-hexane added to the point of cloudiness. Cooling and filtration of the resulting crystals affords 1-(2-dimethylaminoethyl)-3-(α-hydroxybenzyl)-4-hydroxy-4-phenylpiperidine, melting at 157°-158°C.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe resulting mixture is extracted three times with ethyl ether
  3. dry with materialdried over magnesium sulfate
  4. customto give an oil
  5. temperatureCooling
  6. filtrationfiltration of the resulting crystals

Sources & evidence

ORD record
ord-29b7ba895a714c378fc47b6b54271673
Source dataset
uspto-grants-1976_06
Patent number
US03965104

Reaction notes

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