1-(2-Chlorophenyl)piperazinium chloride → 6-Chloro-2-[[4-(2-chlorophenyl)-1-piperazinyl]methyl]-imidazo[1,2-a]pyridine

HRID 1416253Notes

Reaction equation

HRID 1416253 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11]Cl)[N:10]=2)[CH:7]=1.Cl.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:24]3[CH2:23][CH2:22][N:21]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[Cl:14])[CH2:26][CH2:25]3)[N:10]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 30170151-(2-Chlorophenyl)piperazinium chlorideHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 193671316-Chloro-2-[[4-(2-chlorophenyl)-1-piperazinyl]methyl]-imidazo[1,2-a]pyridine

Procedure

Following the general procedure of Example 11 and making noncritical variations, 6-chloro-2-(chloromethyl)imidazo[1,2-α]pyridine (Example 4. Step 1; 0.289 g) and 1-(2-chlorophenyl)piperazine monohydrochloride (Aldrich; 0.381 g) give, after crystallization from ethyl acetate/hexane, 0.2423 g of the title compound; mp 123-123.5° C.; MS m/z 360; IR (mineral oil) 1325, 1475, 1039, 2818, 2810 cm-1 ; 1H NMR (CDCl3) δ2.77, 3.12, 3.79, 6.96, 7.04, 7.12, 7.21, 7.34. 7.52. 8.14.

Workup

  1. customgive
  2. customafter crystallization from ethyl acetate/hexane, 0.2423 g of the title compound

Sources & evidence

ORD record
ord-44505909b0144cf5b34417bfdabbfb4a
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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