Methylamine → HCID 14326774, compound

HRID 2291940Notes

Reaction equation

HRID 2291940 reaction equation
ClCCl.[Cl:4][C:5]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([S:15]([N:18]3[CH2:23][CH2:22][CH:21](OS(C4C=CC(C)=CC=4)(=O)=O)[CH2:20][CH2:19]3)(=[O:17])=[O:16])[C:9]=2[CH:8]=[CH:7][N:6]=1.[CH3:35][NH2:36]>CO>[Cl:4][C:5]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([S:15]([N:18]3[CH2:23][CH2:22][CH:21]([NH:36][CH3:35])[CH2:20][CH2:19]3)(=[O:17])=[O:16])[C:9]=2[CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 6344DichloromethaneHCID 21278384HCID 21278384, compound

Product 1

HCID 14326774HCID 14326774, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To 50 ml of dichloromethane were added 4.0 g of the thus obtained 1-(1-chloro-5-isoquinolinesulfonyl)-4-p-toluenesulfonyloxypiperidine and 1 ml of a 40% methylamine solution in methanol. The mixture was heated at 70° C. for 6 hours in a sealed vessel. Then, the dichloromethane was removed under reduced pressure to obtain an oily residue. The thus obtained oily residue was subjected to purification by silica gel column chromatography (Wacogel C-200, 100 g; solvent: a 5% methanol solution in chloroform) to obtain 2.28 g of 1-(1-chloro-5-isoquinolinesulfonyl)-4-methylaminopiperidine [Compound (94)] in a yield of 71%. Compound (94) was analyzed to give the following data.

Workup

  1. customThen, the dichloromethane was removed under reduced pressure
  2. customto obtain an oily residue
  3. customThe thus obtained oily residue was subjected to purification by silica gel column chromatography (Wacogel C-200, 100 g

Sources & evidence

ORD record
ord-2ca7804284954d6ebd6c7967dfe7d132
Source dataset
uspto-grants-1989_01
Patent number
US04798897

Reaction notes

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