Triethylamine → HCID 22934159, compound

HRID 2251892Notes

Reaction equation

HRID 2251892 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:10][OH:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(=O)([O-])O.[Na+]>ClCCl>[S:23]([O:11][CH2:10][CH2:9][C:8]1[CH:12]=[CH:13][CH:14]=[C:6]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:7]=1)(=[O:25])(=[O:24])[CH3:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 574734173-Pyrrolidinophenethyl Alcohol

Product 1

HCID 22934159HCID 22934159, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Pyrrolidinophenethyl alcohol was dissolved in dichloromethane (20 ml). Triethylamine (3.7 ml, 26.7 ml) and methanesulfonyl chloride (1.9 ml, 24.5 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), suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain 3-pyrrolidinophenethyl mesylate in the form of a white solid (5.13 g, 87%).

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), suitable fractions
  4. customwere collected
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d885acfafcdc4b0ab878f6f0f8b1357b
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

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