1-(2-Fluorophenyl)piperazine Hydrochloride → 6-Chloro-2-[[4-(2-fluorophenyl)-1-piperazinyl]methyl]-imidazo[1,2-a]pyridine

HRID 1416267Notes

Reaction equation

HRID 1416267 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.[F: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[F:14])[CH2:26][CH2:25]3)[N:10]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 27346981-(2-Fluorophenyl)piperazine HydrochlorideHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 193671076-Chloro-2-[[4-(2-fluorophenyl)-1-piperazinyl]methyl]-imidazo[1,2-a]pyridineYield 53.2%

Procedure

Following the general procedure of Example 11 and making non-critical variations, 6-chloro-2-(chloromethyl)imidazo[1,2-α]pyridine (Example 4, Step 1; 0.294 g) and 1-(2-fluorophenyl)piperazine hydrochloride (Aldrich; 0.366 g) are converted to 0.268 g of the title compound after chromatography on silica gel using methanol/dichloromethane (6/94) and crystallization from ethyl acetate/hexane; mp 107-108° C.; MS m/z 344, 346; IR (mineral oil) 1501, 1221, 752, 1335, 927 cm-1 ; 1H NMR (CDCl3) δ2.76, 3.13, 3.78, 6.95, 7.03, 7.12, 7.52, 8.14.

Sources & evidence

ORD record
ord-732b5158f1e743a4b21c1711430719f0
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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