Iodoethane → (1-Ethylpiperidin-3-yl)methyl 4-methylbenzenesulfonate

HRID 2113467Notes

Reaction equation

HRID 2113467 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][O:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:3]1.[CH2:20](I)[CH3:21].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>C(#N)C>[CH2:20]([N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][O:9][S:10]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)(=[O:12])=[O:11])[CH2:3]1)[CH3:21]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 131727084Toluene-4-sulfonic acid piperidin-3-ylmethyl ester, hydrochloride

Product 1

HCID 57656762(1-Ethylpiperidin-3-yl)methyl 4-methylbenzenesulfonateYield 4.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1 g (3.2. mmol) toluene-4-sulfonic acid piperidin-3-ylmethyl ester, hydrochloride, 1.02 g (7 mmol) ethyl iodide (commercially available) and 0.6 g (10 mmol) sodium carbonate in 20 mL acetonitrile was shaken at 65° C. over night. Sodium hydrogencarbonate aq. was added and the mixture was extracted with DCM. The combined organic fractions were evaporated to dryness and the residue was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/NEt3. The combined product fractions were evaporated to yield 40 mg (4%) of the title compound as yellow oil. MS(m/e): 298 (MH+).

Workup

  1. extractionthe mixture was extracted with DCM
  2. customThe combined organic fractions were evaporated to dryness
  3. customthe residue was purified by preparative HPLC on reversed phase
  4. washeluting with a gradient
  5. customformed from acetonitrile/water/NEt3
  6. customThe combined product fractions were evaporated

Sources & evidence

ORD record
ord-5a4d576890b54284b61aa14c21726f61
Source dataset
uspto-grants-2008_10
Patent number
US07432255B2

Reaction notes

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