N,N-Dimethyltetrahydro-2H-pyran-4-amine → N,N-dimethyl-N-(4-(((2-(4-methylphenyl)-6,7-dihydro-5H-benzocyclohepten-8-yl)carbonyl)amino)benzyl)tetrahydro-2H-pyran-4-aminium chloride

HRID 1387978Notes

Reaction equation

HRID 1387978 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][CH2:15][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]([CH3:38])[CH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>CN(C=O)C>[Cl-:1].[CH3:30][N+:31]([CH3:38])([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:13][CH2:14][CH2:15][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][O:35][CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 10176150N,N-Dimethyltetrahydro-2H-pyran-4-amineHCID 10525117N-(4-chloromethylphenyl)-2-(4-methylphenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxamide

Product 1

HCID 183789N,N-dimethyl-N-(4-(((2-(4-methylphenyl)-6,7-dihydro-5H-benzocyclohepten-8-yl)carbonyl)amino)benzyl)tetrahydro-2H-pyran-4-aminium chlorideYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-(4-chloromethylphenyl)-2-(4-methylphenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxamide (9.38 g, 23.3 mmol) in DMF (50 ml) was dropwise added a solution of N,N-dimethyl-N-tetrahydropyran-4-ylamine (4.5 g, 35.0 mmol) in DMF (50 ml). Under nitrogen atmosphere, the mixture was stirred for 23 hours. The solvent was evaporated to give powder, which was washed with acetone and dried. The resulting colorless powder was recrystallized from ethanol to give N,N-dimethyl-N-(4-(((2-(4-methylphenyl)-6,7-dihydro-5H-benzocyclohepten-8-yl)carbonyl)amino)benzyl)-N-(4-tetrahydropyranyl)-ammonium chloride (Compound 248) (10.6 g, 86%) as colorless powder.

Workup

  1. customThe solvent was evaporated
  2. customto give powder, which
  3. washwas washed with acetone
  4. customdried
  5. customThe resulting colorless powder was recrystallized from ethanol

Sources & evidence

ORD record
ord-704dbbe375c14ab8a740ca8b3fa01be2
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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