Sodium Hydroxide → HCID 21409837, compound

HRID 1283534Notes

Reaction equation

HRID 1283534 reaction equation
Cl.[N+:2]([C:5]1[CH:26]=[CH:25][C:8]([C:9]([NH:11][CH2:12][C:13]2([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:10])=[CH:7][CH:6]=1)([O-])=O.[OH-].[Na+].O.NN>O.C(O)C.[Ni]>[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][CH2:12][C:13]2([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:10])=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 86733842HCID 86733842, compound

Product 1

HCID 21409837HCID 21409837, compoundYield 57.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 1-[1-(p-nitrobenzamidomethyl) cyclohexyl]piperidine hydrochloride (2 g.) in water (20 ml) was made alkaline with 5N NaOH and the suspension extracted with chloroform (3 × 30 ml.). The combined chloroform extracts were dried (anhyd. Na2SO4) and evaporated to give a yellow solid (1.7 g.). To a stirred solution of this in ethanol (100 ml) containing Raney Nickel in suspension was added dropwise a solution of hydrazine hydrate (5 ml) in ethanol (5 ml) over 30 mins. The suspension was stirred for a further 31/2 hrs., the suspension was heated to boiling for 30 mins. and filtered through Hyflo. The filtrate was evaporated to dryness and the white solid which formed was crystallised from benzene to give 1-[1-(p-aminobenzamidomethyl) cyclohexyl]piperidine (0.95 g. 50%), m.p. 160-163°.

Workup

  1. extractionthe suspension extracted with chloroform (3 × 30 ml.)
  2. dry with materialThe combined chloroform extracts were dried (anhyd. Na2SO4)
  3. customevaporated
  4. customto give a yellow solid (1.7 g.)
  5. temperature, the suspension was heated
  6. waitto boiling for 30 mins
  7. filtrationand filtered through Hyflo
  8. customThe filtrate was evaporated to dryness
  9. customthe white solid which formed
  10. customwas crystallised from benzene

Sources & evidence

ORD record
ord-202ff3a473424cfa97138868c0463bd3
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

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