N-Ethylpiperidine → 1-(N-(7-(4-methylphenyl)-2,3-dihydro-1-benzoxepin-4-carbonyl)-4-amino-benzyl)-1-ethylpiperidinium chloride

HRID 1277106Notes

Reaction equation

HRID 1277106 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.[CH2:30]([N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[CH3:31]>CN(C)C=O>[Cl-:1].[CH3:29][C:26]1[CH:27]=[CH:28][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:7]=[CH:8][C:3]([CH2:2][N+:32]5([CH2:30][CH3:31])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]5)=[CH:4][CH:5]=4)=[O:11])=[CH:18][C:17]=3[CH:19]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 13007N-EthylpiperidineHCID 18472316N-(4-chloromethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

Product 1

HCID 184725481-(N-(7-(4-methylphenyl)-2,3-dihydro-1-benzoxepin-4-carbonyl)-4-amino-benzyl)-1-ethylpiperidinium chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-chloromethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (0.18 g) and 1-ethylpiperidine (0.31 ml) in dimethylformamide (5 ml) were stirred at 50° C. over night. The solvent was evaporated, and to the residue was added ethyl acetate. Precipitated crude crystal was filtered, which were recrystallized from ethanol-ethyl acetate to give 1-(N-(7-(4-methylphenyl)-2,3-dihydro-1-benzoxepin-4-carbonyl)-4-amino-benzyl)-1-ethylpiperidinium chloride (Compound 98) (0.17 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-ethyl acetate

Sources & evidence

ORD record
ord-b8590909c6cc4cb89ef6714d702231e8
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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