N-Methylpiperidine → HCID 22990120, compound

HRID 1169370Notes

Reaction equation

HRID 1169370 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)=[CH:17][CH:18]=3)[CH2:13]2)=[O:11])=[CH:5][CH:4]=1.[CH3:29][N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>CN(C)C=O>[Br-:1].[CH3:29][N+:30]1([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][C:10]([N:12]3[CH2:21][CH2:20][C:19]4[C:14](=[CH:15][C:16]([C:22]5[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=5)=[CH:17][CH:18]=4)[CH2:13]3)=[O:11])=[CH:5][CH:4]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 12291N-MethylpiperidineHCID 22989949HCID 22989949, compound

Product 1

HCID 22990120HCID 22990120, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-bromomethylphenylacetyl)-7-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline (0.2 g) and 1-methylpiperidine (0.17 ml) in dimethylformamide (5 ml) was stirred overnight at room temperature under a nitrogen atmosphere. The reaction mixture was evaporated to remove the solvent and was mixed with ethyl acetate, and the precipitate was collected by filtration. The precipitate was dissolved in ethanol, and the solvent was evaporated to obtain 1-methyl-1-(4-((7-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl)carbonylmethyl)benzyl)piperidinium bromide (compound 31) (0.24 g) as a colorless amorphous substance.

Workup

  1. customThe reaction mixture was evaporated
  2. customto remove the solvent
  3. additionwas mixed with ethyl acetate
  4. filtrationthe precipitate was collected by filtration
  5. dissolutionThe precipitate was dissolved in ethanol
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b7a438ef687b44c3bb4b04256c3149f6
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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