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

HRID 362911
Notes
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Reaction equation

HRID 362911 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6329MethylamineHCID 675952155-fluoro-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Product 1

HCID 675945745-methylamino-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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

  1. temperatureAfter cooling
  2. extractionextracted with AcOEt
  3. washThe extract was washed with H2O
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes