Chloroform → 6-[3-{N-2-(4-methoxymethoxy-1-piperidinyl)ethyl-N-cyclooctylmethylamino}-thiocarbonylaminopropoxy]carbostyril

HRID 2257906Notes

Reaction equation

HRID 2257906 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH:12]=[CH:11]2)=[C:2]=[S:3].[CH:19]1([N:27](C)[CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][CH:33]([O:36][CH2:37][O:38][CH3:39])[CH2:32][CH2:31]2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[CH:41](Cl)(Cl)Cl>>[CH3:39][O:38][CH2:37][O:36][CH:33]1[CH2:32][CH2:31][N:30]([CH2:29][CH2:28][N:27]([CH:4]([N:1]=[C:2]=[S:3])[CH2:5][CH2:6][O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH:12]=[CH:11]3)[CH2:19][CH:26]2[CH2:41][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[CH2:35][CH2:34]1

Participants

4

Reactant 3

HCID 6212ChloroformHCID 229236916-(3-Isothiocyanatopropoxy)carbostyrilHCID 229236961-[2-(Cyclooctyl-methylamino)ethyl]-4-methoxymethoxypiperidine

Product 1

HCID 1317193726-[3-{N-2-(4-methoxymethoxy-1-piperidinyl)ethyl-N-cyclooctylmethylamino}-thiocarbonylaminopropoxy]carbostyril

Procedure

A solution of 0.22 g of 6-(3-isothiocyanato-propoxy)carbostyril and 0.3 g of 1-[2-(cyclooctyl-methylamino)ethyl]-4-methoxymethoxypiperidine in 30 ml of chloroform was stirred at room temperature for 5 hours. The solvent was removed by distillation under reduced pressure. The resulting residue was purified by a silica gel column chromatography (eluant: 3% methanol/dichloromethane) to obtain 0.36 g of 6-[3-{N-2-(4-methoxymethoxy-1-piperidinyl)ethyl-N-cyclooctylmethylamino}-thiocarbonylaminopropoxy]carbostyril.

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. customThe resulting residue was purified by a silica gel column chromatography (eluant: 3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-c89a11840c874e2faa2138c84c0e92dc
Source dataset
uspto-grants-1997_08
Patent number
US05658926

Reaction notes

Loading…