Triethylamine → Methanesulfonic acid 1-cyclopentyl-piperidin-4-yl ester

HRID 272846Notes

Reaction equation

HRID 272846 reaction equation
[CH:1]1([N:6]2[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[S:20](Cl)([CH3:23])(=[O:22])=[O:21]>C(Cl)Cl>[CH:1]1([N:6]2[CH2:7][CH2:8][CH:9]([O:12][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:10][CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 217027851-Cyclopentylpiperidin-4-ol

Product 1

HCID 86601898Methanesulfonic acid 1-cyclopentyl-piperidin-4-yl esterYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Cyclopentyl-4-hydroxypiperidine (1 g, 5.91 mmol), DCM (10 ml) and triethylamine (0.91 ml, 6.5 mmol) were cooled to 0-5° C. and mesyl chloride (0.46 ml, 5.91 mmol) was added dropwise under N2. The reaction was allowed to warm to room temperature and stirred for 1 hour. The reaction was quenched with sat. NaHCO3 (20 ml) and the aqueous phase extracted with DCM (2×5 ml). The combined organic extracts were dried over MgSO4, filtered, washed with DCM and concentrated in vacuo to give the title compound (1.38 g, 95%) as a pale yellow oil.

Workup

  1. customThe reaction was quenched with sat. NaHCO3 (20 ml)
  2. extractionthe aqueous phase extracted with DCM (2×5 ml)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. washwashed with DCM
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e65579e9f22947bab86731c5d3bfee80
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

Loading…