4-Toluenesulfonyl chloride → 1-Piperidinesulfonamide,4-hydroxy-(7CI,8CI)

HRID 1868085Notes

Reaction equation

HRID 1868085 reaction equation
C1(C)C=CC([S:7](Cl)(=[O:9])=[O:8])=CC=1.[OH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.CC[N:21](C(C)C)C(C)C>ClCCl>[OH:12][CH:13]1[CH2:18][CH2:17][N:16]([S:7]([NH2:21])(=[O:9])=[O:8])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 79341Piperidin-4-olHCID 81531Diisopropylethylamine

Product 1

HCID 450805901-Piperidinesulfonamide,4-hydroxy-(7CI,8CI)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of p-toluenesulfonyl chloride (39.28 mmol) in dichloromethane (160 mL) was added 4-hydroxypiperidine (40.07 mmol) dropwise, followed by 13.7 ml i-Pr2NEt. The mixture was stirred at room temperature for 3 h. Solvent was removed under vacuum and crude product was purified with flash column chromatography to yield 4-hydroxypiperidin sulfonamide (I).

Workup

  1. customSolvent was removed under vacuum and crude product
  2. customwas purified with flash column chromatography

Sources & evidence

ORD record
ord-85abc7f806084d48b4e302b62ef8ca0e
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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