Sodium Bicarbonate → 3-(5-Benzoyl-2-nitro-benzylamino)-N-cyclohexyl-N-methyl-propionamide

HRID 390195Notes

Reaction equation

HRID 390195 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][C:12]([N+:17]([O-:19])=[O:18])=[C:13]([CH:16]=1)[CH:14]=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][CH2:21][CH2:22][C:23]([N:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[CH3:26])=[O:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[C:1]([C:9]1[CH:10]=[CH:11][C:12]([N+:17]([O-:19])=[O:18])=[C:13]([CH:16]=1)[CH2:14][NH:20][CH2:21][CH2:22][C:23]([N:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[CH3:26])=[O:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 167934313-Amino-N-cyclohexyl-N-methyl-propionamideHCID 198160555-Benzoyl-2-nitrobenzaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 5-benzoyl-2-nitro-benzaldehyde (10 g, 0.0390 mol), a known compound (which may be prepared as disclosed in European Patent EP 371564) and 3-amino-N-cyclohexyl-N-methyl-propionamide (7.5 g, 0.0410 mol) in 1,2-dichloroethane (250 mL) was stirred at room temperature under nitrogen. Sodium triacetoxyborohydride (8.7 g, 0.0410 mol) was added, and the reaction mixture was stirred for 6 h at room temperature. Saturated NaHCO3 solution (200 mL) was then added. The organic layer was separated, dried, and evaporated. The resulting residue was purified by column chromatography on silica gel (eluent: 99:1 CH2Cl2:MeOH). The purest fractions were combined, and the solvent was evaporated to yield a residue.

Workup

  1. stirringthe reaction mixture was stirred for 6 h at room temperature
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated
  5. customThe resulting residue was purified by column chromatography on silica gel (eluent: 99:1 CH2Cl2:MeOH)
  6. customthe solvent was evaporated
  7. customto yield a residue

Sources & evidence

ORD record
ord-8b014ed121054edbab6e0d75a5ccdb6f
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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