4-(Dimethylamino)cyclohexan-1-one → HCID 15480021, compound

HRID 1387979Notes

Reaction equation

HRID 1387979 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]([CH3:39])[CH:32]1[CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]1>CN(C)C=O>[Cl-:1].[CH3:30][N+:31]([CH3:39])([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)[CH:32]1[CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 103745454-(Dimethylamino)cyclohexan-1-oneHCID 18472316N-(4-chloromethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

Product 1

HCID 15480021HCID 15480021, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-(4-chloromethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (214 mg, 0.530 mmol) in N,N-dimethylformamide (1 ml) was dropwise added a solution of 4-dimethylaminocyclohexanone (112 mg, 0.795 mmol) in N,N-dimethylformamide (1 ml). Under nitrogen atmosphere, the mixture was stirred for 14 hours. The solvent was evaporated to give crude product, which was washed with ether to give N,N-dimethyl-N-(4-(((7-(4-methylphenyl)-2,3-dihydro-1-benzoxepin-4-yl)carbonyl)-amino)benzyl)-N-(4-oxocyclohexyl)ammonium chloride (Compound 249) (305 mg) as colorless powder.

Workup

  1. customThe solvent was evaporated
  2. customto give crude product, which
  3. washwas washed with ether

Sources & evidence

ORD record
ord-b6c88e6beeb544fb850bcaf06d94b408
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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