N-Methylpiperidine → 1-(N-(7-(4-methylphenyl)-2,3-dihydro-1-benzoxepin-4-carbonyl)-4-aminobenzyl)-1-methylpiperidinium chloride

HRID 2228124Notes

Reaction equation

HRID 2228124 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:13][CH2:14][O:15][C:16]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)=[CH:19][C:17]=3[CH:18]=2)=[O:11])=[CH:5][CH:4]=1.[CH3:30][N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>CN(C)C=O>[Cl-:1].[CH3:29][C:26]1[CH:25]=[CH:24][C:23]([C:20]2[CH:21]=[CH:22][C:16]3[O:15][CH2:14][CH2:13][C:12]([C:10]([NH:9][C:6]4[CH:5]=[CH:4][C:3]([CH2:2][N+:31]5([CH3:30])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]5)=[CH:8][CH:7]=4)=[O:11])=[CH:18][C:17]=3[CH:19]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 12291N-MethylpiperidineHCID 18472316N-(4-chloromethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

Product 1

HCID 184724551-(N-(7-(4-methylphenyl)-2,3-dihydro-1-benzoxepin-4-carbonyl)-4-aminobenzyl)-1-methylpiperidinium chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-chloromethylphenyl)-7—(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (0.15 g) and 1-methylpiperidine (0.14 ml) in dimethylformamide (15 ml) was stirred at room temperature over night. The solvent was evaporated, and to the residue was added ethyl acetate. Precipitated crude crystal was filtered, which were recrystallized from ethanol-diethylether to give 1—(N-(7—(4-methylphenyl)-2,3-dihydro-1-benzoxepin-4-carbonyl)-4-aminobenzyl)-1-methylpiperidinium chloride (Compound 97) (0.15 g) as colorless crystals.

Workup

  1. customThe solvent was evaporated
  2. additionto the residue was added ethyl acetate
  3. customPrecipitated crude crystal
  4. filtrationwas filtered
  5. customwhich were recrystallized from ethanol-diethylether

Sources & evidence

ORD record
ord-db094d5af14f48efa4138db01577fdd1
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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