Thiophene → 3-(2-Amino-5-benzoyl-benzylamino)-N-cyclohexyl-N-methyl-propionamide

HRID 390262Notes

Reaction equation

HRID 390262 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][C:12]([N+:29]([O-])=O)=[C:13]([CH:28]=1)[CH2:14][NH:15][CH2:16][CH2:17][C:18]([N:20]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH3:21])=[O:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S1C=CC=C1>CO.[Pt]>[NH2:29][C:12]1[CH:11]=[CH:10][C:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:28][C:13]=1[CH2:14][NH:15][CH2:16][CH2:17][C:18]([N:20]([CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)[CH3:21])=[O:19]

Participants

5

Reactant 2

HCID 8030ThiopheneHCID 177564853-(5-Benzoyl-2-nitro-benzylamino)-N-cyclohexyl-N-methyl-propionamide

Product 1

HCID 586251113-(2-Amino-5-benzoyl-benzylamino)-N-cyclohexyl-N-methyl-propionamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

3-(5-Benzoyl-2-nitro-benzylamino)-N-cyclohexyl-N-methyl-propionamide (0.01 mol) was converted into its corresponding free base. A mixture of the free base (0.01 mol) in methanol (200 mL) was hydrogenated under atmospheric conditions, with 5% Pt/C (2 g) as a catalyst in the presence of 4% thiophene solution (1 mL). After uptake of H2 (3 equiv.), the catalyst was filtered off and the filtrate was evaporated. Toluene was added to the residue, then evaporated again to yield the title compound as a residue.

Workup

  1. filtrationAfter uptake of H2 (3 equiv.), the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additionToluene was added to the residue
  4. customevaporated again

Sources & evidence

ORD record
ord-d253574510c04f4d9a3a83b2d380ca40
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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