2-Chloromethyl-imidazo(1,2-A)pyridine → HCID 6469918, compound

HRID 1416304Notes

Reaction equation

HRID 1416304 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[CH:11]=1.Cl.Cl.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1>>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]2[CH2:26][CH2:25][N:24]([CH2:2][C:3]3[N:4]=[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][N:6]4[CH:11]=3)[CH2:23][CH2:22]2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 9576142-Chloromethyl-imidazo(1,2-A)pyridineHCID 12212341Piperazine, 1-(4-chlorophenyl)-, hydrochloride (1:2)

Product 1

HCID 6469918HCID 6469918, compoundYield 51%

Procedure

Following the general procedure of Example 38, Step 2, and making non-critical variations, 2-(chloromethyl)imidazo[1,2-a]pyridine (Example 2, Step 1; 0.25 g) and 1-(4-chlorophenyl)piperazine dihydrochloride (Aldrich; 0.45 g) give 0.25 g of the title compound after chromatography on silica gel using methanol/dichloromethane (4/96), pooling of the appropriate fractions, and crystallization from dichloromethane/ethyl ether; mp 138-139° C.; IR (mineral oil) 1339, 1498, 765, 814, 1223 cm-1 ; 1H NMR (CDCl3) δ2.75, 3.20, 3.79, 6.79, 7.17, 7.56, 7.57, 8.08.

Sources & evidence

ORD record
ord-1b4ff10fd47541d7a3fb03d5169599ea
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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