Triethylamine → 1-Methylpiperidin-4-yl methanesulfonate

HRID 64056

Reaction equation

HRID 64056 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.CCN(CC)CC.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:16][S:17]([O:8][CH:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 660484-Piperidinol, 1-methyl-

Product 1

HCID 41906811-Methylpiperidin-4-yl methanesulfonateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Methylpiperidin-4-ol (4 g, 34.7 mmol) was dissolved in CH2Cl2 (70 ml) at 0° C. followed by the addition of Et3N (10 ml, 69.4 mmol, 2 eq.) and methanesulfonyl chloride (2.7 ml, 34.7 mmol, 1 eq.). The mixture was stirred at RT for 3 h and quenched and extracted as in Intermediate Example 5(a). The solvent was distilled off to afford the crude product (6.7 g).

Workup

  1. customquenched
  2. extractionextracted as in Intermediate Example 5(a)
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-95d2427a2ebc434081e05472c18fdde3
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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