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

HRID 565930Notes

Reaction equation

HRID 565930 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 (0.18g) and 1-ethylpiperidine (0.31ml) in dimethylformamide (5ml) 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) (0.17g) 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-cb528625f7bd45e3af32f79c1a3a4a69
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

Loading…