Chloroform → HCID 14326827, compound

HRID 2291956Notes

Reaction equation

[CH2:1]([N:7]([CH2:21][CH2:22]OS(C1C=CC(C)=CC=1)(=O)=O)[S:8]([C:11]1[C:12]2[CH:13]=[CH:14][N:15]=[CH:16][C:17]=2[CH:18]=[CH:19][CH:20]=1)(=[O:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C(Cl)(Cl)Cl>C(O)C>[CH2:1]([N:7]([CH2:21][CH2:22][N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[S:8]([C:11]1[C:12]2[CH:13]=[CH:14][N:15]=[CH:16][C:17]=2[CH:18]=[CH:19][CH:20]=1)(=[O:9])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 80 °C

Procedure

In 30 ml of ethanol were dissolved 5.47 g of N-hexyl-N-(2-p-toluenesulfonyloxyethyl)-5-isoquinolinesulfonamide and 2.85 g of piperidine, and the solution was heated in a pressure vessel at 80° C. for 3 hours. To the mixture obtained was added 100 ml of chloroform, and the resultant mixture was washed with 100 ml of water and dried with anhydrous magnesium sulfate. The chloroform was removed under reduced pressure to obtain a residue. The residue thus obtained was subjected to purification by silica gel column chromatography (Wacogel C-200, solvent: 3% methanol solution in chloroform) to obtain 3.6 g of N-hexyl-N-(2-piperidinoethyl)-5-isoquinolinesulfonamide [Compound (45)]. Compound (45) was analyzed to give the following data.

Workup

customTo the mixture obtained
washthe resultant mixture was washed with 100 ml of water
dry with materialdried with anhydrous magnesium sulfate
customThe chloroform was removed under reduced pressure
customto obtain a residue
customThe residue thus obtained
customwas subjected to purification by silica gel column chromatography (Wacogel C-200, solvent: 3% methanol solution in chloroform)

Sources & evidence

ORD record: ord-d880b5459702460a9189e8d7d13d5f27
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04798897

Reaction notes

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