1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 19367138, compound

HRID 1416288Notes

Reaction equation

HRID 1416288 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.[F:13][C:14]([F:28])([F:27])[C:15]1[CH:16]=[C:17]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:18]=[CH:19][CH:20]=1>CO.ClCCl>[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:17]4[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:27])([F:28])[F:13])[CH:16]=4)[CH2:26][CH2:25]3)[N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 19367138HCID 19367138, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Following the general procedure of Example 39, Step 2, and making non-critical variations, 6-chloro-2-(chloromethyl)imidazo[1,2-α]pyridine (Example 4, Step 1; 0.2982 g) and 1-[3-(trifluoromethyl)phenyl]piperazine (Aldrich; 0.34 mL) are converted to product, followed by chromatography on silica gel using methanol/dichlormethane (2/98). Crystallization from ethyl acetate and then from ethyl acetate/dichloromethane gives 0.053 g of the title compound; mp 145-145.5° C.; MS m/z 394; IR (mineral oil) 1117, 1163, 1451, 1073, 1339 cm-1 ; 1H NMR (CDCl3) δ2.75, 3.28, 3.78, 7.12, 7.34, 7.52, 7.54, 8.14.

Workup

  1. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-66be0539d2c9481aa54abcaf9050e76b
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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