Hydrochloric Acid → 4-Benzamido-1-(4-phenyl-4-hydroxybutyl)piperidine

HRID 437241Notes

Reaction equation

HRID 437241 reaction equation
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:20])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO.[OH-].[Na+]>[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[OH:20])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 100892541-(3-Benzoylpropyl)-4-benzamidopiperidine

Product 1

HCID 214305654-Benzamido-1-(4-phenyl-4-hydroxybutyl)piperidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Benzamido-(4-phenyl-4-oxobutyl)piperidine (3.4 g.) was dissolved in methanol (125 ml.) and a solution of sodium borohydride (6.0 g.) in 0.2 N sodium hydroxide (30 ml.) was added at room temperature over a period of 0.5 hours. The resulting mixture was stirred for a further 2 hours and then heated under reflux for 4 hours. The resulting mixture was filtered, the filtrate evaporated almost to dryness and then treated with water (100 ml.). The colourless solid was filtered off, washed with water, dried, dissolved in a small amount of ethanolic hydrogen chloride and treated with ether until crystallisation commenced. Filtration and drying gave 1.875 g. of the hydrochloride of the title compound, m.p. 221° C. (Found: C, 68.1; H, 7.4; N, 7.3. C22H28N2O2.HCl requires C, 67.9; H, 7.5; N, 7.2%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. filtrationThe resulting mixture was filtered
  4. customthe filtrate evaporated almost to dryness
  5. additiontreated with water (100 ml.)
  6. filtrationThe colourless solid was filtered off
  7. washwashed with water
  8. customdried
  9. dissolutiondissolved in a small amount of ethanolic hydrogen chloride
  10. additiontreated with ether until crystallisation
  11. filtrationFiltration
  12. customdrying
  13. customgave 1.875 g

Sources & evidence

ORD record
ord-297fba93c64e4981b7fc2b43e36094e7
Source dataset
uspto-grants-1977_06
Patent number
US04029801

Reaction notes

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