Water → Methanesulfonic acid 1-pyrimidin-2-yl-piperidin-4-yl ester

HRID 1853372Notes

Reaction equation

HRID 1853372 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:8][CH2:9][CH:10]([O:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 202340981-(Pyrimidin-2-yl)piperidin-4-ol

Product 1

HCID 86673125Methanesulfonic acid 1-pyrimidin-2-yl-piperidin-4-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 1-Pyrimidin-2-yl-piperidin-4-ol (WO2008/8895 A1), (100 mg; 0.55 mmol) and triethylamine (233 μL, 1.67 mmol) in dry dichloromethane (1 mL), was added methanesulfonyl chloride (52 μL, 0.67 mmol). The reaction mixture was stirred at room temperature for 5 hours. Water was added. After extraction with dichloromethane, the combined organic extracts were dried over sodium sulfate and concentrated to afford a crude product that was used in the next step without further purification.

Workup

  1. extractionAfter extraction with dichloromethane
  2. dry with materialthe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-eaf8a611c1f04dc9a9b81630d20d065e
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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