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

HRID 362934Notes

Reaction equation

HRID 362934 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:28]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[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].[CH2:36]([N:40]=[C:41]=[O:42])[CH2:37][CH2:38][CH3:39]>C(Cl)(Cl)Cl>[CH2:32]([N:31]([CH2:34][CH3:35])[C:28]1[CH:29]=[CH:30][C:2]([NH:1][C:41]([NH:40][CH2:36][CH2:37][CH2:38][CH3:39])=[O:42])=[C:3]([CH:27]=1)[C:4]([NH:6][CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:12][CH2:13]1)=[O:5])[CH3:33]

Participants

4

Reactant 2

HCID 8110Butyl isocyanateHCID 675958752-amino-5-diethylamino-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Product 1

HCID 99379445-diethylamino-2-(N'-n-butylureido)-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Step 3): To a solution of 2-amino-5-diethylamino-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide (593 mg, 1.259 mmol) in CHCl3 (20 ml) was added n-butylisocyanate (374 mg, 3.779 mmol). The solution was refluxed overnight and evaporated. The residue was purified by column chromatography on silica gel to give 5-diethylamino-2-(N'-n-butylureido)-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide, 366 mg (51%): mp 158°-160° C.;

Workup

  1. temperatureThe solution was refluxed overnight
  2. customevaporated
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4c598af756fb412a9e118c64e89fc2b8
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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