Diethylamine → 5-diethylamino-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

HRID 362932Notes

Reaction equation

HRID 362932 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:31]([O-:33])=[O:32])=[C:6]([CH:30]=1)[C:7]([NH:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:8].[CH2:34]([NH:36][CH2:37][CH3:38])[CH3:35]>CN(C=O)C>[CH2:34]([N:36]([CH2:37][CH3:38])[C:2]1[CH:3]=[CH:4][C:5]([N+:31]([O-:33])=[O:32])=[C:6]([CH:30]=1)[C:7]([NH:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:8])[CH3:35]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 675952155-fluoro-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Product 1

HCID 675967725-diethylamino-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamideYield 97.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step 1): To a solution of 5-fluoro-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide (prepared according to Preparation 24) (2.1 g, 4.68 mmol) in DMF (30 ml) was added diethylamine (1.46 ml, 14.06 mmol). The solution was refluxed overnight and evaporated under reduced pressure to give 5-diethylamino-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide (2.28 g, 97.5%): mp 167°-168° C.

Workup

  1. temperatureThe solution was refluxed overnight
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b40438f0619340cab86ad06a22542635
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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