Water → HCID 14022353, compound

HRID 1732347Notes

Reaction equation

HRID 1732347 reaction equation
[BH4-].[Li+].[C:3]([N:6]1[CH2:11][CH2:10][CH:9]([O:12][CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14](OCC)=[O:15])[CH2:8][CH2:7]1)(=[O:5])[CH3:4].[H][H].O>O1CCCC1>[C:3]([N:6]1[CH2:11][CH2:10][CH:9]([O:12][CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][OH:15])[CH2:8][CH2:7]1)(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 4148881Lithium borohydrideHCID 14022352HCID 14022352, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14022353HCID 14022353, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (3.24 g.) was added portionwise to a solution of α-(N-acetyl-4-piperidinoxy) phenylacetic acid, ethyl ester (11.2 g.) in dry tetrahydrofuran (200 ml.). When the hydrogen evolution had subsided the reaction mixture was heated under reflux for 4 hours. Water was added to the cooled solution, the solvent evaporated in vacuo, then the residue taken up in chloroform (200 ml.) and washed with dilute hydrochloric acid, water and brine. The chloroform extract was dried (MgSO4) and the solvent evaporated in vacuo. Thin layer chromatography analysis of the product indicated that reduction was incomplete, therefore the product in tetrahydrofuran (100 ml.) was treated with a further quantity of lithium borohydride (3.24 g.) and heated under reflux for 4 hours. The reaction mixture was treated as above to give N-acetyl-4-(2-hydroxy-1-phenyl-ethoxy) piperidine (9.5 g.) as an oil which solidified on standing. A sample crystallized from ether and had an m.p. of 92°-94° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customthe solvent evaporated in vacuo
  4. washwashed with dilute hydrochloric acid, water and brine
  5. extractionThe chloroform extract
  6. dry with materialwas dried (MgSO4)
  7. customthe solvent evaporated in vacuo
  8. additionthe product in tetrahydrofuran (100 ml.) was treated with a further quantity of lithium borohydride (3.24 g.)
  9. temperatureheated
  10. temperatureunder reflux for 4 hours
  11. additionThe reaction mixture was treated as above

Sources & evidence

ORD record
ord-8afb9cbb766f4d81be55f4fa85316e76
Source dataset
uspto-grants-1980_12
Patent number
US04237138

Reaction notes

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