1-Benzoyl-3-[1-(3-nitrobenzyl)piperid-4-yl]urea → 1-Benzoyl-3-[1-(3-aminobenzyl)piperid-4-yl]urea

HRID 3888Notes

Reaction equation

HRID 3888 reaction equation
[C:1]([NH:9][C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=2)[CH2:15][CH2:14]1)=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd]>[C:1]([NH:9][C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[CH:21]=2)[CH2:15][CH2:14]1)=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 129423121-Benzoyl-3-[1-(3-nitrobenzyl)piperid-4-yl]ureaHCID 178418361HCID 178418361, compound

Product 1

HCID 129423061-Benzoyl-3-[1-(3-aminobenzyl)piperid-4-yl]ureaYield 46.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1-Benzoyl-3-[1-(3-nitrobenzyl)piperid-4-yl]urea 4.47 g (from Example 13) was hydrogenated with 5% Pd/C (0.5 g) at atmospheric pressure and room temperature until no more hydrogen was taken up. The catalyst was filtered and the filtrate evaporated. The residue was dissolved in water and basified with 0.880 ammonia. The precipitated solid was filtered, washed well with water, dried, treated with charcoal, and evaporated to give the title compound, (1.9 gms). This was recrystallised from ethanolic HCl to give the dihydrochloride salt, monohydrate, m.p. 194°-195° C.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate evaporated
  3. dissolutionThe residue was dissolved in water and basified with 0.880 ammonia
  4. filtrationThe precipitated solid was filtered
  5. washwashed well with water
  6. customdried
  7. additiontreated with charcoal
  8. customevaporated

Sources & evidence

ORD record
ord-229294ec89824edba85133b93bb6a360
Source dataset
uspto-grants-1988_02
Patent number
US04722930

Reaction notes

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