4-Toluenesulfonyl chloride → HCID 21278384, compound

HRID 2291939Notes

Reaction equation

HRID 2291939 reaction equation
[Cl:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12]([N:15]3[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]3)(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>N1C=CC=CC=1>[Cl:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12]([N:15]3[CH2:16][CH2:17][CH:18]([O:21][S:28]([C:25]4[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=4)(=[O:30])=[O:29])[CH2:19][CH2:20]3)(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 14326772HCID 14326772, compound

Product 1

HCID 21278384HCID 21278384, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 40 ml of pyridine were added 3.11 g of the thus obtained 1-(1-chloro-5-isoquinolinesulfonyl)-4-hydroxypiperidine and 3.81 g of p-toluenesulfonyl chloride. The resulting mixture was stirred at a temperature of 15° C. to 20° C. for 24 hours. To the reaction mixture was added 100 g of ice water, followed by extraction twice with 100 ml each of dichloromethane. The dichloromethane layer was dried with anhydrous magnesium sulfate and the dichloromethane was removed under reduced pressure to obtain 4.46 g of 1-(1-chloro-5-isoquinolinesulfonyl)-4-p-toluenesulfonyloxypiperidine.

Workup

  1. extractionfollowed by extraction twice with 100 ml each of dichloromethane
  2. dry with materialThe dichloromethane layer was dried with anhydrous magnesium sulfate
  3. customthe dichloromethane was removed under reduced pressure

Sources & evidence

ORD record
ord-db2257cc27434cd9bcdddd72c47b90ba
Source dataset
uspto-grants-1989_01
Patent number
US04798897

Reaction notes

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