Ammonia → HCID 21482389, compound

HRID 1415427Notes

Reaction equation

HRID 1415427 reaction equation
[CH:1]1([CH2:4][C:5](=O)[CH:6]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:7]([CH3:12])([N+:9]([O-])=O)[CH3:8])[CH2:3][CH2:2]1.N>C(O)C.[Ni]>[ClH:19].[CH:1]1([CH:4]2[CH2:5][CH:6]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[C:7]([CH3:12])([CH3:8])[NH:9]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 57289127HCID 57289127, compound

Product 1

HCID 21482389HCID 21482389, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

15.3 G of 1-cyclopropyl-3-(p-chlorophenyl)-4-methyl-4-nitropentanone in 200 ml of ethanol saturated with ammonia are hydrogenated for 7 hours 30 minutes under 100 atmospheres at 120° C in the presence of 8 g of Raney Nickel. After filtration and concentration of the filtrate in vacuo, the residue is diluted with ethanol-ether (50:50) and the base is neutralised with hydrogen chloride in ether. The precipitate so obtained is filtered off, washed with ether and recrystallized from isopropanol to give 9.5 g of 2-cyclopropyl-4-(p-chlorophenyl)-5,5-dimethyl-pyrrolidine hydrochloride as white crystals. Melting point = 235°-240° C.

Workup

  1. filtrationAfter filtration and concentration of the filtrate in vacuo
  2. additionthe residue is diluted with ethanol-ether (50:50)
  3. customThe precipitate so obtained
  4. filtrationis filtered off
  5. washwashed with ether
  6. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-dc630f8f5f8f4517a819ae8601dcbb19
Source dataset
uspto-grants-1977_01
Patent number
US04005103

Reaction notes

Loading…