Ammonium Chloride → 4-Methyl-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]pyridazino[4,5-b]indolizin-1-amine

HRID 704086Notes

Reaction equation

HRID 704086 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[C:9]3[N:14]([C:6]=2[C:5]([CH3:15])=[N:4][N:3]=1)[CH:13]=[CH:12][CH:11]=[CH:10]3.[CH3:16][N:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[CH2:22][CH2:23][NH2:24].[Cl-].[NH4+]>>[CH3:15][C:5]1[N:4]=[N:3][C:2]([NH:24][CH2:23][CH2:22][CH:18]2[CH2:19][CH2:20][CH2:21][N:17]2[CH3:16])=[C:7]2[C:6]=1[N:14]1[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]1)=[CH:8]2

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 157133121-Chloro-4-methylpyridazino[4,5-b]indolizine

Product 1

HCID 157133294-Methyl-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]pyridazino[4,5-b]indolizin-1-amine

Procedure

Following the procedure of Example 1, reaction of one equivalent of 1-chloro-4-methylpyridazino[4,5-b]indolizine, ten equivalents of 2-(1-methyl-2-pyrrolidinyl)ethylamine and one equivalent of ammonium chloride under reflux in a nitrogen atmosphere for 3 to 4 hours gave the title compound as the free base after removal of excess amine in vacuo and treatment of the residue with boiling ethyl acetate. The solid collected upon filtration was converted to the hydrochloride salt (methanol/ethereal HCl/ether), mp 169° C.

Workup

  1. temperatureunder reflux in a nitrogen atmosphere for 3 to 4 hours

Sources & evidence

ORD record
ord-58b54f67740a41858f44b5cf6b921848
Source dataset
uspto-grants-1991_01
Patent number
US04985560

Reaction notes

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