Methyl iodide → SB 227122

HRID 565972Notes

Reaction equation

HRID 565972 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[CH2:17][CH2:16][CH2:15][C:14]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([CH2:27][N:28]([CH:30]5[CH2:35][CH2:34][O:33][CH2:32][CH2:31]5)[CH3:29])=[CH:23][CH:22]=4)=[O:19])=[CH:13][C:12]=3[CH:36]=2)=[CH:4][CH:3]=1.[CH3:37][I:38]>CN(C)C=O>[I-:38].[CH3:29][N+:28]([CH3:37])([CH2:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:18]([C:14]2[CH2:15][CH2:16][CH2:17][C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=4)=[CH:36][C:12]=3[CH:13]=2)=[O:19])=[CH:22][CH:23]=1)[CH:30]1[CH2:31][CH2:32][O:33][CH2:34][CH2:35]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 30134302-(4-methylphenyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)phenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxamide

Product 1

HCID 9873888SB 227122

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-methylphenyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)phenyl)-6,7-dihydro-5 H-benzocycloheptene-8-carboxamide (0.11 g) and methyl iodide (0.02 ml) in dimethylformamide (4 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 was recrystallized from ethanol-ethyl acetate to give N,N-dimethyl-N-(4-((2-(4-methylphenyl)-6,7-dihydro-5 H-benzocyclohepten-8-yl)carbonyl)aminobenzyl)-N-(4-tetrahydropyranyl)ammonium iodide (Compound 220) (0.13 g) as pale yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-2fa52f8957c44cc38aeb947a8824a2bf
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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