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

HRID 362911Notes

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].[CH3:34][NH2:35].CO.O>CN(C=O)C>[CH3:34][NH:35][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]

Participants

Conditions

Temperature: 180 °C

Procedure

Step 1): A mixture of 5-fluoro-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide (2.68 g, 6 mmol) and 40% methylamine in MeOH (5 ml, 64 mmol) in DMF (30 ml) was heated in a sealed tube at 180° C. for 7 hours. After cooling, the reaction mixture was poured into H2O and extracted with AcOEt. The extract was washed with H2O, dried over MgSO4 and evaporated, followed by crystallization from EtOH to give 5-methylamino-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide, 2.28 g (83%): mp 185° C.

Workup

temperatureAfter cooling
extractionextracted with AcOEt
washThe extract was washed with H2O
dry with materialdried over MgSO4
customevaporated
customfollowed by crystallization from EtOH

Sources & evidence

ORD record: ord-64f9dcbe33bf40a08edac349431e5495
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05872115

Reaction notes

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