Methanesulfonyl chloride → HCID 22934161, compound

HRID 2251894Notes

Reaction equation

HRID 2251894 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([CH2:11][CH2:12][OH:13])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].C(=O)([O-])O.[Na+]>ClCCl>[S:26]([O:13][CH2:12][CH2:11][C:10]1[CH:9]=[CH:8][C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[CH:15][CH:14]=1)(=[O:28])(=[O:27])[CH3:25]

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 135928032-(4-Morpholinophenyl)ethanol

Product 1

HCID 22934161HCID 22934161, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Morpholinophenethyl alcohol (2.35 g, 11.3 mmol) was dissolved in dichloromethane (20 ml). Diisopropylethylamine (2.60 ml, 14.8 mmol) and methanesulfonyl chloride (1.11 ml, 14.8 mmol) were added to the obtained solution at 0° C., and they were stirred for 4 hours. 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 (3:1) and then with them (1:1) as the eluents, suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain 4-morpholinophenethyl mesylate in the form of a white solid (2.60 g, 81%).

Workup

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

Sources & evidence

ORD record
ord-91c790f5238046ea9ba58c09a449558e
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

Loading…