Pyridine → HCID 86628178, compound

HRID 910465Notes

Reaction equation

HRID 910465 reaction equation
[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:13][S:14]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][C@@H:18]1[CH3:23])(=[O:16])=[O:15].N1C=CC=CC=1>C(Cl)Cl>[CH3:13][S:14]([N:17]1[CH2:22][CH2:21][N:20]([C:2]([Cl:1])=[O:4])[CH2:19][C@@H:18]1[CH3:23])(=[O:15])=[O:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 66617741HCID 66617741, compound

Product 1

HCID 86628178HCID 86628178, compoundYield 154.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Second step: To a stirred solution of carbonic acid ditrichloromethyl ester (triphosgene) (560 mg, 1.88 mmol) in CH2Cl2 (10 mL) at −78° C., was added a solution of (S)-1-methanesulfonyl-2-methyl-piperazine (838 mg, 4.70 mmol) and pyridine (0.74 mL, 9.4 mmol) in CH2Cl2 (10 mL) over 1 hour. The temperature was raised to RT, and stirring was continued over night. The organic phase was washed with H2O, dried over Na2SO4. Concentration under vacuo and flash chromatography (SiO2, EtOAc/H, 1:1) yielded 0.70 g (62%) of (S)-4-methanesulfonyl-3-methyl-piperazine-1-carbonyl chloride as a light yellow solid.

Workup

  1. waitwas continued over night
  2. washThe organic phase was washed with H2O
  3. dry with materialdried over Na2SO4
  4. concentrationConcentration under vacuo and flash chromatography (SiO2, EtOAc/H, 1:1)

Sources & evidence

ORD record
ord-00c9b2a34d404855a9275382ffdf3d7b
Source dataset
uspto-grants-2011_09
Patent number
US08022099B2

Reaction notes

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