Methyl iodide → HCID 10747204, compound

HRID 2228166Notes

Reaction equation

HRID 2228166 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[CH:15][C:16]4[CH2:22][CH2:21][CH2:20][C:19]([C:23]([NH:25][C:26]5[CH:31]=[CH:30][C:29]([CH2:32][N:33]([CH:35]6[CH2:40][CH2:39][O:38][CH2:37][CH2:36]6)[CH3:34])=[CH:28][CH:27]=5)=[O:24])=[CH:18][C:17]=4[CH:41]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:42][I:43]>CN(C)C=O>[I-:43].[CH3:34][N+:33]([CH3:42])([CH2:32][C:29]1[CH:28]=[CH:27][C:26]([NH:25][C:23]([C:19]2[CH2:20][CH2:21][CH2:22][C:16]3[CH:15]=[CH:14][C:13]([C:10]4[CH:9]=[CH:8][C:7]([N:1]5[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]5)=[CH:12][CH:11]=4)=[CH:41][C:17]=3[CH:18]=2)=[O:24])=[CH:31][CH:30]=1)[CH:35]1[CH2:36][CH2:37][O:38][CH2:39][CH2:40]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 10626473HCID 10626473, compound

Product 1

HCID 10747204HCID 10747204, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2—(4-piperidinophenyl)-N-(4—((N-tetrahydropyran-4-yl-N-methylamino)methyl)phenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxamide (0.2 g) and methyl iodide (0.025 ml) in dimethylformamide (10 ml) was stirred at room temperature over night. The solvent was evaporated, and the residue was purified with silica gel column (chloroform/methanol) to give crude crystals, which were recrystallized from ethanol-hexane to give dimethyl-(N-(2—(4-piperidinophenyl)-6,7-dihydro-5H-benzocyclo-heptene-8-carbonyl)-4-aminobenzyl)-4-tetrahydropyranyl-ammonium iodide (Compound 225) (0.15 g) as pale brown crystals.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified with silica gel column (chloroform/methanol)
  3. customto give crude crystals, which
  4. customwere recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-48addbda068e47d599c824a9c1df993e
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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