Hydrochloric Acid → 2-(4-Chlorophenyl)-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]-3H-imidazo [4,5-b]pyridine-3-acetamide hydrochloride hydrate

HRID 2073067Notes

Reaction equation

HRID 2073067 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:20][CH2:21][CH2:22][CH:23]3[CH2:27][CH2:26][CH2:25][N:24]3[CH3:28])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.Cl.C(OC(C)C)(C)C>C(O)(C)C>[OH2:19].[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:20][CH2:21][CH2:22][CH:23]3[CH2:27][CH2:26][CH2:25][N:24]3[CH3:28])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 143903682-(4-Chlorophenyl)-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]-3H-imidazo [4,5-b]pyridine-3-acetamide

Product 1

HCID 230374182-(4-Chlorophenyl)-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]-3H-imidazo [4,5-b]pyridine-3-acetamide hydrochloride hydrateYield 185.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of crude 2-(4-chlorophenyl)-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]-3H-imidazo[4,5-b]pyridine-3-acetamide (3.96 g, 0.0100 mole) in hot isopropyl alcohol was acidified with hydrogen chloride in isopropyl alcohol. Isopropyl ether was added to the cloud point. Upon cooling to room temperature, a solid precipitated. The solid was collected by filtration, rinsed with isopropyl ether, and dried under high vacuum to give 4.2 g (86%) of title compound, mp 171°-175° C.

Workup

  1. customa solid precipitated
  2. filtrationThe solid was collected by filtration
  3. washrinsed with isopropyl ether
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-9dc286d176b74172926f690251d85b22
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

Loading…