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

HRID 1730353Notes

Reaction equation

HRID 1730353 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 0.2N 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 (100ml.). 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 (100ml.)
  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-928434dfc9dc49ef8da22c3aa5aff858
Source dataset
uspto-grants-1976_11
Patent number
US03992389

Reaction notes

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