Ammonium Chloride → N-[4-(3-Azabicyclo[3.2.2]non-3-yl)butyl]-4-methylpyridazino[4,5-b]indolizin-1-amine

HRID 704085Notes

Reaction equation

HRID 704085 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.[CH:16]12[CH2:24][CH2:23][CH:20]([CH2:21][CH2:22]1)[CH2:19][N:18]([CH2:25][CH2:26][CH2:27][CH2:28][NH2:29])[CH2:17]2.[Cl-].[NH4+]>>[CH:20]12[CH2:23][CH2:24][CH:16]([CH2:22][CH2:21]1)[CH2:17][N:18]([CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:2]1[N:3]=[N:4][C:5]([CH3:15])=[C:6]3[N:14]4[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]4)=[CH:8][C:7]=13)[CH2:19]2

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 135110814-(3-Azabicyclo[3.2.2]non-3-yl)butylamineHCID 157133121-Chloro-4-methylpyridazino[4,5-b]indolizine

Product 1

HCID 15713328N-[4-(3-Azabicyclo[3.2.2]non-3-yl)butyl]-4-methylpyridazino[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, three equivalents of 4-(3-azabicyclo[3.2.2]non-3-yl)butylamine and one equivalent of ammonium chloride at 145° C. under nitrogen overnight gave the title compound as the free base after flash column chromatography (silica gel, 4:1 methylene chloride:methanol to 100% methanol containing ammonium hydroxide). This was converted to the dihydrochloride salt and recrystallized from ethanol, mp 257°-258° C.

Sources & evidence

ORD record
ord-b38a9ef66f7842efb38e0f542cdf553a
Source dataset
uspto-grants-1991_01
Patent number
US04985560

Reaction notes

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