4-Methoxybenzenesulfonyl chloride → HCID 5192268, compound

HRID 1954084Notes

Reaction equation

HRID 1954084 reaction equation
Cl.[NH:2]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:3]1[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.O1CCOCC1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>O>[CH3:7][O:6][C:4]([CH:3]1[CH2:8][CH2:9][CH2:10][CH2:11][N:2]1[S:33]([C:30]1[CH:29]=[CH:28][C:27]([O:26][CH3:25])=[CH:32][CH:31]=1)(=[O:35])=[O:34])=[O:5]

Participants

6

Reactant 4

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 13246231Methyl Pipecolinate Hydrochloride

Product 1

HCID 5192268HCID 5192268, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Methyl pipecolinate hydrochloride (10.0 g, 55.6 mmol), triethylamine (14.1 g, 19.4 mL, 139.2 mmol, 2.5 equiv), 1,4-dioxane (75 mL), and water (75 mL) are stirred at room temperature and then p-methoxyphenylsulfonyl chloride (13.8 g, 66.8 mmol, 1.2 equiv) is added. The resulting solution is stirred at room temperature overnight. The solution is then poured into water and extracted with CH2Cl2. The combined organic extracts are dried (Na2SO4) and concentrated to an oil under reduced pressure. Purification of the oil is accomplished by chromatography on silica gel using 7/3 hexane/EtOAc as the eluent. The product is obtained as a colorless oil which solidified upon standing.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined organic extracts are dried (Na2SO4)
  3. concentrationconcentrated to an oil under reduced pressure
  4. customPurification of the oil
  5. customThe product is obtained as a colorless oil which

Sources & evidence

ORD record
ord-99e22aebe90e4162a4d6f489f23599c6
Source dataset
uspto-grants-2000_09
Patent number
US06121272

Reaction notes

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