Ethanol → HCID 12788384, compound

HRID 2295457Notes

Reaction equation

HRID 2295457 reaction equation
[C:1]1([CH:7]2[C:12](=[O:13])[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].C(O)C.[Na+].[Cl-]>C1C=CC=CC=1>[C:1]1([C@H:7]2[C@H:12]([OH:13])[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 11947944HCID 11947944, compound

Product 1

HCID 12788384HCID 12788384, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 0.9 g of the free base, 3-phenyl-4-piperidone of Example 50c, above, 0.19 g of sodium borohydride and 15 ml of absolute ethanol is stirred at room temperature for 6 hours under a nitrogen atmosphere. The mixture is then treated with 25 ml of saturated aqueous NaCl solution and extracted with dichloromethane. The combined organic extracts are washed with saturated aqueous NaCl solution, dried over anhydrous Na2 SO4 and concentrated in vacuo to a gum which TLC shows to be a mixture of cis and trans isomers, with the trans isomer predominant. Trituration of this material with benzene gives a well formed solid which is filtered off after allowing the mixture to stand 18 hours. The solid is washed with benzene and then hexane, and dried in vacuo to afford a solid, m.p. s 99°, 115°-127° C., which TLC showed contained only a small amount of the cis isomer. This material is taken up in 10 ml of boiling benzene, filtered, and boiled down to a volume of approximately 5 ml of solution to afford a solid of trans-3-phenyl-4-piperidinol, m.p. s 125.5°, 127°-128.5°, which TLC showed to be pure trans isomer.

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic extracts are washed with saturated aqueous NaCl solution
  3. customdried over anhydrous Na2 SO4
  4. concentrationconcentrated in vacuo to a gum which TLC
  5. additiona mixture of cis and trans isomers
  6. customTrituration of this material with benzene gives a well formed solid which
  7. filtrationis filtered off
  8. washThe solid is washed with benzene
  9. dry with materialhexane, and dried in vacuo
  10. customto afford a solid, m.p.
  11. customs 99°, 115°-127° C.
  12. filtrationfiltered

Sources & evidence

ORD record
ord-b7f4a5cf81564222a83ed51fa443560f
Source dataset
uspto-grants-1984_01
Patent number
US04424357

Reaction notes

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