1-Phenylpiperazine → HCID 53630882, compound

HRID 446190Notes

Reaction equation

HRID 446190 reaction equation
[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]Br)[CH:15]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].[C:22]1([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:31]4[CH2:32][CH2:33][N:28]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:29][CH2:30]4)[CH:15]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2]

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 516892Sodium BicarbonateHCID 58797754HCID 58797754, compound

Product 1

HCID 53630882HCID 53630882, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-cyano-6-(3-bromomethylbenzyloxy)benzothiazole (1 g, 2.8 mmol) in 20 mL of dichloromethane was added 1-phenylpiperazine (1.7 mL, 11.2 mmol) dropwise. The resultant solution was stirred at RT for 30 minutes. Then, 20 mL of saturated sodium bicarbonate solution was added. After partition, the aqueous phase was extracted with 20 mL of dichloromethane. The organic extracts were combined, washed with water twice and dried over sodium sulfate. The solvent was removed and the residue was purified by flash chromatography using 1% methanol in dichloromethane. 594 mg of product was obtained.

Workup

  1. customAfter partition
  2. extractionthe aqueous phase was extracted with 20 mL of dichloromethane
  3. washwashed with water twice
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3ff0b12fbafb49e3933e4f1323277a52
Source dataset
uspto-grants-2013_07
Patent number
US08476450B2

Reaction notes

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