N-Methylpiperidine → 1-Methyl-1-(4-((7-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl)carbonylamino)benzyl)piperidinium chloride

HRID 1169368Notes

Reaction equation

HRID 1169368 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][N:14]([C:18]([NH:20][C:21]4[CH:28]=[CH:27][C:24]([CH2:25][Cl:26])=[CH:23][CH:22]=4)=[O:19])[CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:29][N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>CN(C)C=O>[Cl-:26].[CH3:29][N+:30]1([CH2:25][C:24]2[CH:27]=[CH:28][C:21]([NH:20][C:18]([N:14]3[CH2:13][CH2:12][C:11]4[C:16](=[CH:17][C:8]([C:5]5[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=5)=[CH:9][CH:10]=4)[CH2:15]3)=[O:19])=[CH:22][CH:23]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 12291N-MethylpiperidineHCID 229900814-(7-(4-Methylphenyl)-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonylamino)benzyl chloride

Product 1

HCID 229899451-Methyl-1-(4-((7-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl)carbonylamino)benzyl)piperidinium chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(7-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonylamino)benzyl chloride (0.2 g) and 1-methyl piperidine (0.19 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 recrystallized from ethanol to obtain 1-methyl-1-(4-((7-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl)carbonylamino)benzyl)piperidinium chloride (compound 29) (0.23 g) as colorless crystals.

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. customThe precipitate was recrystallized from ethanol

Sources & evidence

ORD record
ord-e13bc54846ba494da91abd93dd712e89
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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