Butyl isocyanate → 5-nitro-2-(N'-n-butylureido)-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

HRID 362937Notes

Reaction equation

HRID 362937 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][C:3]=1[C:4]([NH:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:5].[CH2:34]([N:38]=[C:39]=[O:40])[CH2:35][CH2:36][CH3:37]>C(Cl)(Cl)Cl>[N+:31]([C:28]1[CH:29]=[CH:30][C:2]([NH:1][C:39]([NH:38][CH2:34][CH2:35][CH2:36][CH3:37])=[O:40])=[C:3]([CH:27]=1)[C:4]([NH:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:10][CH2:9]1)=[O:5])([O-:33])=[O:32]

Participants

4

Reactant 2

HCID 8110Butyl isocyanateHCID 67594998HCID 67594998, compound

Product 1

HCID 675962945-nitro-2-(N'-n-butylureido)-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Step 1): To a solution of 2amino-5nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide (Preparation 28) (1.2 g, 2.69 mmol) in CHCl3 (15 ml) was added n-butylisocyanate (802 mg, 8.09 mmol). After the solution was refluxed for 24 hours, the solvent was evaporated. The residue was purified by column chromatography on silica gel to give 5-nitro-2-(N'-n-butylureido)-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide, 1.1 g (75%).

Workup

  1. temperatureAfter the solution was refluxed for 24 hours
  2. customthe solvent was evaporated
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-67e54d16f71e46a18e7a0d14068e89a1
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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