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

HRID 1169369Notes

Reaction equation

HRID 1169369 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.[CH2:29]([N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[CH3:30]>CN(C)C=O>[Cl-:26].[CH2:29]([N+:31]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)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[CH3:30]

Participants

4

Reactant 2

HCID 13007N-EthylpiperidineHCID 229900814-(7-(4-Methylphenyl)-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonylamino)benzyl chloride

Product 1

HCID 229900851-Ethyl-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-ethylpiperidine (0.21 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 to obtain 1-ethyl-1-(4-((7-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl)carbonylamino)benzyl)piperidinium chloride (compound 30) (0.24 g) as a light red, 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

Sources & evidence

ORD record
ord-f9e5530041944498a0b1addcbf243e24
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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