Methanol → HCID 18695590, compound

HRID 1586457Notes

Reaction equation

HRID 1586457 reaction equation
C[N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH2:22][CH3:23])[N:13]=2)=[O:11])[CH2:4][CH2:3]1.CO>ClC(OC(Cl)C)=O>[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH2:22][CH3:23])[N:13]=2)=[O:11])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 887MethanolHCID 15485211HCID 15485211, compound

Product 1

HCID 18695590HCID 18695590, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 5213051-Chloroethyl chloroformateSolvent

Procedure

A solution of N-(1-methyl-4-piperidyl)methyl-1-n-propylindazole-3-carboxamide (2.00 g) obtained in Example 7 in α-chloroethyl chloroformate (8 ml) was stirred at 70° C. for 6 hours, then methanol (20 ml) was added, and the mixture was heated under reflux for 2 hours. The reaction solution was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=90:10:1) to give the title compound (0.40g) as a yellow oily substance. Yield=21%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. distillationThe reaction solution was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=90:10:1)

Sources & evidence

ORD record
ord-57c9c13eb1744a55bc78f3fcff5b6ece
Source dataset
uspto-grants-1999_08
Patent number
US05945434

Reaction notes

Loading…