Water → HCID 58181280, compound

HRID 1465503Notes

Reaction equation

HRID 1465503 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][CH2:25][OH:26])=[CH:20][CH:19]=3)=[N:14][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36].O>ClCCl>[CH3:34][S:35]([O:26][CH2:25][CH2:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][CH2:16][C:13]2[CH:12]=[CH:11][C:10]([N:7]3[CH2:6][CH2:5][N:4]([C:1](=[O:3])[CH3:2])[CH2:9][CH2:8]3)=[CH:15][N:14]=2)=[CH:23][CH:22]=1)(=[O:37])=[O:36]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58181333HCID 58181333, compound

Product 1

HCID 58181280HCID 58181280, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)ethanol (354.1 mg, 1.002 mmol) in dichloromethane (14 ml) were added triethylamine (0.25 ml, 1.5 mmol) and methanesulfonyl chloride (0.116 ml, 1.67 mmol), and the mixture was stirred at room temperature for 45 mins. Water was added to the reaction mixture, and the mixture was extracted twice with dichloromethane. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to dryness to give 2-(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)ethyl methanesulfonate (415.0 mg, yield 96.0%) as a slightly brown solid.

Workup

  1. extractionthe mixture was extracted twice with dichloromethane
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-dee1360e31654e7aabe181377087ad76
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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