3-Amino-1-propanol → 6-[3-(3-Hydroxypropyl)aminopropoxy]carbostyril

HRID 1856764Notes

Reaction equation

HRID 1856764 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH:10]=[CH:9]2.[NH2:17][CH2:18][CH2:19][CH2:20][OH:21]>CO>[OH:21][CH2:20][CH2:19][CH2:18][NH:17][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH:10]=[CH:9]2

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 142894806-(3-Chloropropoxy)carbostyril

Product 1

HCID 572709646-[3-(3-Hydroxypropyl)aminopropoxy]carbostyril

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-(3-chloropropoxy)carbostyril (5.0 g) and 3-amino-1-propanol (24 ml) in methanol (25 ml) is heated at 100° C. for 4 hours in an autoclave. The mixture is concentrated under reduced pressure to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol:aqueous ammonia=70:10:1), and recrystallized from methanol-diethyl ether to give 6-[3-(3-hydroxypropyl)aminopropoxy]carbostyril(4.4 g) as a white powder.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customto remove the solvent
  3. customthe residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol:aqueous ammonia=70:10:1)
  4. customrecrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-6e8e732cde10467fbfe89574096deabc
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

Loading…