Chloroform → HCID 86614354, compound

HRID 2265156Notes

Reaction equation

HRID 2265156 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].C(Cl)(Cl)Cl.[CH3:17][N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH:20]([CH2:31][OH:32])[CH2:19]1>C(OCC)(=O)C>[CH3:8][S:9]([O:32][CH2:31][CH:20]1[CH:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19]1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68427102HCID 68427102, compound

Product 1

HCID 86614354HCID 86614354, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C. 0.45 mL of triethylamine and 0.17 mL of methanesulfonyl chloride were added to chloroform (5 mL) solution of 237 mg of (3SR,4RS)-(1-methyl-4-o-tolylpiperidin-3-yl)-methanol obtained in Production Example 33-1. This was stirred at 0° C. for 50 minutes, diluted with ethyl acetate, washed with aqueous saturated sodium hydrogencarbonate solution, and dried with anhydrous sodium sulfate, and the solvent was evaporated off under reduced pressure to obtain 321 mg of 1-methyl-4-o-tolylpiperidin-3-ylmethyl methanesulfonate.

Workup

  1. customAt 0° C
  2. customobtained in Production Example 33-1
  3. washwashed with aqueous saturated sodium hydrogencarbonate solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-a520eae66a89492fb0f40942592ad8f2
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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