Thiophene → Cyclohexanecarboxylic acid [2-(2-amino-5-benzoyl-benzylamino)-ethyl]-amide

HRID 390205Notes

Reaction equation

HRID 390205 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:3]=1[CH:4]=O.[NH2:18][CH2:19][CH2:20][NH:21][C:22]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23].S1C=CC=C1>CO.[Pd]>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:3]=1[CH2:4][NH:18][CH2:19][CH2:20][NH:21][C:22]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23]

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 13028009N-(2-aminoethyl)cyclohexanecarboxamideHCID 586251382-Amino-5-benzoylbenzaldehyde

Product 1

HCID 58625175Cyclohexanecarboxylic acid [2-(2-amino-5-benzoyl-benzylamino)-ethyl]-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-amino-5-benzoylbenzaldehyde (0.007 mol) and cyclohexanecarboxylic acid (2-amino-ethyl)-amide (0.007 mol) in methanol was hydrogenated at 50° C. with 10% Pd/C (0.5 g) as a catalyst in the presence of thiophene solution (1 mL). After uptake of H2 gas (1 equiv.) the catalyst was filtered off and the solvent evaporated. The residue was purified by column chromatography over silica gel (Biotage column) (eluent:CH2Cl2:methanol gradient). The desired fractions were collected and the solvent evaporated to yield the title compound as a residue.

Workup

  1. filtrationAfter uptake of H2 gas (1 equiv.) the catalyst was filtered off
  2. customthe solvent evaporated
  3. customThe residue was purified by column chromatography over silica gel (Biotage column) (eluent:CH2Cl2:methanol gradient)
  4. customThe desired fractions were collected
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-e5efc6a90f2f417191b978d0ac3d50a9
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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