Sodium Bicarbonate → HCID 14326757, compound

HRID 2291941Notes

Reaction equation

HRID 2291941 reaction equation
Cl.[CH:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.[C:16](=[O:19])([O-])O.[Na+]>>[CH:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12]([N:3]3[CH2:2][CH2:11][CH2:6][CH:16]([OH:19])[CH2:4]3)(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 13116932Isoquinoline-5-sulfonyl chloride hydrochloride

Product 1

HCID 14326757HCID 14326757, compound

Procedure

In 100 ml of ice water was dissolved 10.6 g of 5-isoquinolinesulfonyl chloride hydrochloride, and the pH of the solution was adjusted to 6 with a saturated aqueous sodium hydrogencarbonate solution, followed by extraction with of 200 ml of dichloromethane. The dichloromethane layer was added dropwise to a 100 ml of dichloromethane solution containing 6.0 g of 3-hydroxypiperidine and 6.0 g of triethylamine over 30 minutes while cooling with ice. The mixture was stirred at a temperature of 15° C. to 20° C. for 3 hours, washed with water, and dried with anhydrous magnesium sulfate. Then, the dichloromethane was removed under reduced pressure to obtain 8.50 g of 1-(5-isoquinolinesulfonyl)-3-hydroxypiperidine.

Workup

  1. extractionfollowed by extraction with of 200 ml of dichloromethane
  2. additionThe dichloromethane layer was added dropwise to a 100 ml of dichloromethane solution
  3. additioncontaining 6.0 g of 3-hydroxypiperidine and 6.0 g of triethylamine over 30 minutes
  4. temperaturewhile cooling with ice
  5. washwashed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThen, the dichloromethane was removed under reduced pressure

Sources & evidence

ORD record
ord-0fe02bb5e20a4b81a7f652afd46b88d0
Source dataset
uspto-grants-1989_01
Patent number
US04798897

Reaction notes

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