Hydrochloric Acid → 4-(Isoquinoline-5-sulfonyl)piperazine-1-carboximidamide

HRID 980013Notes

Reaction equation

HRID 980013 reaction equation
S(O)(O)(=O)=O.[C:6]([N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)(=[NH:8])[NH2:7].[CH:15]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([S:25](Cl)(=[O:27])=[O:26])[C:19]=2[CH:18]=[CH:17][N:16]=1.[OH-].[Na+].Cl>O.O1CCCC1>[C:6]([N:9]1[CH2:14][CH2:13][N:12]([S:25]([C:20]2[C:19]3[CH:18]=[CH:17][N:16]=[CH:15][C:24]=3[CH:23]=[CH:22][CH:21]=2)(=[O:26])=[O:27])[CH2:11][CH2:10]1)(=[NH:7])[NH2:8]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium Hydroxide3×HCID 33716555-Isoquinolinesulfonyl chlorideHCID 155946771052089-53-8

Product 1

HCID 144165144-(Isoquinoline-5-sulfonyl)piperazine-1-carboximidamideYield 87.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 30 ml of water was dissolved 3.9 g of 1-amidinopiperazine sulfate, and 60 ml of tetrahydrofuran solution containing 4.1 g of 5-isoquinolinesulfonyl chloride and 1N sodium hydroxide was added dropwise under cooling with ice so that the pH of the solution maintain the range from 8 to 8.5. After the dropwise addition, the mixture solution was stirred for one hour. The crystalline residue was discarded, and the pH of the aqueous layer was adjusted to 1 with an aqueous diluted hydrochloric acid solution. The crystalline residue was discarded, and the pH of the aqueous layer was adjusted to 13 with a 5N aqueous sodium hydroxide solution. The crystals precipitated were separated by filtration, and the crystalline residue obtained was dissolved with an aqueous diluted hydrochloric acid solution. The pH of the solution was adjusted to 13.5 with a 2N aqueous sodium hydroxide solution. The crystals precipitated were separated by filtration, the crystalline residue was washed with water, methanol and ethylether and condensed to dryness to give 4.84 g of 4-amidino-1-(5-isoquinolinesulfonyl)piperazine, i.e., Compound (44) in a yield of 84%.

Workup

  1. additionwas added dropwise
  2. temperatureunder cooling with ice so that the pH of the solution
  3. temperaturemaintain the range from 8 to 8.5
  4. additionAfter the dropwise addition
  5. customThe crystals precipitated
  6. customwere separated by filtration
  7. customthe crystalline residue obtained
  8. customThe crystals precipitated
  9. customwere separated by filtration
  10. washthe crystalline residue was washed with water, methanol and ethylether and condensed to dryness

Sources & evidence

ORD record
ord-0ae1730c16274ec5b6f045690206b940
Source dataset
uspto-grants-1987_01
Patent number
US04634770

Reaction notes

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