Benzenesulfonyl chloride → Phenylmethyl 4-[(phenylsulfonyl)oxy]-1-piperidinecarboxylate

HRID 1582026Notes

Reaction equation

HRID 1582026 reaction equation
C(N(CC)CC)C.[OH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][CH2:10]1.[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[CH2:18]([O:17][C:15]([N:12]1[CH2:11][CH2:10][CH:9]([O:8][S:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:33])=[O:32])[CH2:14][CH2:13]1)=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Product 1

HCID 85794901Phenylmethyl 4-[(phenylsulfonyl)oxy]-1-piperidinecarboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (17 ml) was added dropwise to a solution of benzyl 4-hydroxy-1-piperidinecarboxylate (28.83 g) in dichloromethane (100 ml) at 0° C. and stirred for 15 minutes. Benzenesulfonyl chloride (14 ml) was added and the reaction allowed to stir at room temperature for 48 h. The mixture was washed with water (50 ml), saturated sodium bicarbonate solution (50 ml), water (50 ml) and brine (50 ml) then dried (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by chromatography (SiO2, 20% ethyl acetate in hexane to 30% ethyl acetate in hexane) to give the title compound (31.88 g, 77%) as a white crystalline solid.

Workup

  1. stirringto stir at room temperature for 48 h
  2. washThe mixture was washed with water (50 ml), saturated sodium bicarbonate solution (50 ml), water (50 ml) and brine (50 ml)
  3. dry with materialthen dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by chromatography (SiO2, 20% ethyl acetate in hexane to 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-20ed185898df4af38af39d9907039a4a
Source dataset
uspto-grants-2004_05
Patent number
US06734189B2

Reaction notes

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