Methanesulfonyl chloride → 4-Pyrrolidinophenethyl mesylate

HRID 2251886

Reaction equation

HRID 2251886 reaction equation
[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([CH2:10][CH2:11][OH:12])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(=O)([O-])O.[Na+]>ClCCl>[S:16]([O:12][CH2:11][CH2:10][C:9]1[CH:13]=[CH:14][C:6]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:7][CH:8]=1)(=[O:18])(=[O:17])[CH3:15]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 124983722-[4-(Pyrrolidin-1-yl)phenyl]ethan-1-ol

Product 1

HCID 229341624-Pyrrolidinophenethyl mesylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Pyrrolidinophenethyl alcohol (16.41 g, 85.9 mmol) was dissolved in dichloromethane (150 ml). Dissopropylethylamine (19.0 ml, 108 ml) and methanesulfonyl chloride (8.40 ml, 108 mmol) were added to the obtained solution at 0° C., and they were stirred overnight. The reaction mixture was distributed into 5% aqueous sodium hydrogencarbonate solution and dichloromethane. The organic layer was dried and the solvent was evaporated under reduced pressure. The residue was subjected to the silica gel column chromatography. After the elution with hexane and ethyl acetate (7:3) as the eluent, suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain 4-pyrrolidinophenethyl mesylate in the form of a white solid (21.14 g, 80%).

Workup

  1. customThe organic layer was dried
  2. customthe solvent was evaporated under reduced pressure
  3. washAfter the elution with hexane and ethyl acetate (7:3) as the eluent, suitable fractions
  4. customwere collected
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-449dc1d5b6e8433f9450fc04471b8628
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Linked notes

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