1-Phenylpiperazine → HCID 59013780, compound

HRID 907567Notes

Reaction equation

HRID 907567 reaction equation
Cl[C:2]1[C:3]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[N:4][S:5][N:6]=1.[C:15]1([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.CO>[C:15]1([N:21]2[CH2:26][CH2:25][N:24]([C:2]3[C:3]([O:7][CH2:8][C:9]4[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=4)=[N:4][S:5][N:6]=3)[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 70961-PhenylpiperazineHCID 59013789HCID 59013789, compound

Product 1

HCID 59013780HCID 59013780, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

4-(4-chloro-[1,2,5]thiadiazol-3-yloxymethyl)-pyridine (50 mg, 0.22 mmol) was dissolved in 200 μL of DMF along with 1-phenylpiperazine (75 μL, 0.49 mmol). The reaction was heated to 70° C. overnight. The reaction mixture was diluted with methanol to a volume of 2 mL and the reaction mixture was purified by reverse phase chromatography, affording 1-phenyl-4-{4-[(pyridin-4-ylmethyl)oxy]-1,2,5-thiadiazol-3-yl}piperazine (7 mg). 1H NMR (DMSO-d6) δ 8.62 (d, 2H), 7.46 (d, 2H), 7.23 (t, 2H), 7.01 (d, 2H), 6.82 (t, 1H), 5.58 (s, 2H), 3.64 (m, 4H), 3.23 (m, 4H) ppm.

Workup

  1. customthe reaction mixture was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-a06a0b0fd04e419bb727d359b1a552fc
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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