1-(methylsulfonyl)isoquinoline → HCID 23035479, compound

HRID 2118972Notes

Reaction equation

HRID 2118972 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CS([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][N:24]=1)(=O)=O>CO>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][N:24]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2924961-(methylsulfonyl)isoquinolineHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 23035479HCID 23035479, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[3-(Piperidinomethyl)phenoxy]propylamine (2.04 g) and 1-methylsulphonylisoquinoline (1.70 g) were fused at 135° C. for 51/4 hours. The cooled reaction mixture was taken up in methanol, filtered, evaporated and subjected to medium pressure column chromatography on silica (chloroform:methanol 1:19-second column using chloroform) to give the title compound (0.56 g) as an oil. This was treated with maleic acid (0.35 g) in warm ethanol to yield, on cooling, 1-[3-[3-(piperidinomethyl)phenoxy]propylamino]isoquinoline dimaleate (0.15 g), m.p. 103°-105° C. (recrystallised from ethanol).

Workup

  1. customwere fused at 135° C. for 51
  2. custom4 hours
  3. customThe cooled reaction mixture
  4. filtrationfiltered
  5. customevaporated
  6. customsubjected to medium pressure column chromatography on silica (chloroform:methanol 1:19-second column using chloroform)

Sources & evidence

ORD record
ord-0d1c8c71711249df8e83c1cd5a079c81
Source dataset
uspto-grants-1987_07
Patent number
US04681883

Reaction notes

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