Thionyl Chloride → 1-Acetyl-4-(6-{2-[4-(chloromethyl)phenyl]ethyl}pyridin-3-yl)piperazine

HRID 1465476Notes

Reaction equation

HRID 1465476 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=3)=[N:14][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].S(Cl)([Cl:28])=O>ClCCl>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[N:14][C:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][Cl:28])=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58181252(4-{2-[5-(4-Acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)methanol

Product 1

HCID 581812881-Acetyl-4-(6-{2-[4-(chloromethyl)phenyl]ethyl}pyridin-3-yl)piperazineYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)methanol (227.0 mg, 0.669 mmol) in dichloromethane (5 ml) was added thionyl chloride (0.096 ml, 1.331 mmol). After stirring at room temperature for 2 hrs, the reaction mixture was concentrated. To the residue was added aqueous sodium carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated to dryness to give 1-acetyl-4-(6-{2-[4-(chloromethyl)phenyl]ethyl}pyridin-3-yl)piperazine (234.8 mg, yield 98.1%) as a silghtly yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionTo the residue was added aqueous sodium carbonate solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9c8eab7fef6241f884a72652cabb66cc
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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