Methyl isothiocyanate → 4-[2-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-N-methyl-1-piperidine-carbothioamide

HRID 1058636Notes

Reaction equation

HRID 1058636 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16][CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[CH3:23][N:24]=[C:25]=[S:26]>C(Cl)Cl>[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:25](=[S:26])[NH:24][CH3:23])[CH2:19][CH2:18]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 18668800HCID 18668800, compound

Product 1

HCID 186687914-[2-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-N-methyl-1-piperidine-carbothioamideYield 89.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 0.50 g of 4-amino-1-[2-(4-piperidyl)ethyl]-1H-imidazo[4,5-c]-quinoline and 0.37 g of methylisothiocyanate in 10 ml of methylene chloride was stirred at room temperature for 1 hour, and then the precipitated crystals were collected by filtration to give 0.56 g of colorless crystals. Recrystallization from a mixture of methylene chloride and methanol gave colorless crystals having the melting point of from 216 to 218° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-a278047b29e84d688d8806fba915afe2
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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