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

HRID 272843Notes

Reaction equation

HRID 272843 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C(N(CC)CC)C.[S:18](Cl)([CH3:21])(=[O:20])=[O:19]>C(Cl)Cl>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 796811-Isopropylpiperidin-4-ol

Product 1

HCID 86601897Methanesulfonic acid 1-isopropyl-piperidin-4-yl esterYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Isopropyl-4-hydroxypiperidine (1 g, 6.98 mmol), DCM (10 ml) and triethylamine (1.08 ml, 7.68 mmol) were cooled to 0-5° C. and mesyl chloride (0.54 ml, 6.98 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 (1.55 g, 100%) 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-f5aca03f90fc4620afb15493884ab6b3
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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