Dichloromethane → HCID 14013553, compound

HRID 1904812Notes

Reaction equation

HRID 1904812 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.ClCCl.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>O>[CH3:28][S:29]([O:17][CH:14]1[CH2:15][CH2:16][N:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH2:12][CH2:13]1)(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14518091HCID 14518091, compound

Product 1

HCID 14013553HCID 14013553, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 90 parts of 1-[(4-methylphenyl)sulfonyl]-4-piperidinol, 37.5 parts of N,N-diethylethanamine and 1300 parts of dichloromethane was added dropwise a solution of 42.3 parts of methanesulfonyl chloride in 130 parts of dichloromethane (exothermic reaction: temperature rose to 35° C.). Upon completion, stirring was continued for 2 hours at room temperature. Water was added and the layers were separated. The organic phase was washed with water, dried, filtered and evaporated. The residue was suspended in 2,2'-oxybispropane. The product was filtered off and dried, yielding 116 parts (100%) of 1-[(4-methylphenyl)sulfonyl]-4-piperidinol methanesulfonate (ester); mp. 168.5°-175.3° C. (5).

Workup

  1. customthe layers were separated
  2. washThe organic phase was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-a9367d786df341e7abd634e3ae797a5a
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

Loading…