Triethylamine → 1,1-dioxo-N-[4-[4-(piperidin-1-ylmethyl)pyrazol-1-yl]oxybutyl]-1,2-benzothiazol-3-amine

HRID 232026Notes

Reaction equation

HRID 232026 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[N:10][N:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[S:29](=[O:37])(=[O:36])[N:28]=1>C(Cl)Cl>[N:1]1([CH2:7][C:8]2[CH:9]=[N:10][N:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:27]3[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[S:29](=[O:36])(=[O:37])[N:28]=3)[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64783Pseudosaccharin chlorideHCID 200307904-(4-Piperidinomethylpyrazol-1-yloxy)butylamine

Product 1

HCID 1785271931,1-dioxo-N-[4-[4-(piperidin-1-ylmethyl)pyrazol-1-yl]oxybutyl]-1,2-benzothiazol-3-amineYield 29.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.5 g of 4-(4-piperidinomethylpyrazol-1-yloxy)butylamine and 1.4 g of triethylamine are dissolved in 50 ml of methylene chloride. A solution of 2.8 g of 3-chlorobenzoisothiazole 1,1-dioxide in 15 ml of methylene chloride is then added dropwise. After standing for 3 hours at room temperature, the reaction mixture is washed with water, the organic phase is evaporated down and the residue is chromatographed over neutral Al2O3 (activity level III), using methylene chloride as the mobile phase. 1.7 g of the title compound are obtained, the product being crystallized from ether.

Workup

  1. washthe reaction mixture is washed with water
  2. customthe organic phase is evaporated down
  3. customthe residue is chromatographed over neutral Al2O3 (activity level III)

Sources & evidence

ORD record
ord-2dfd0f29ad2d434bb1dce4d38d5b1c7f
Source dataset
uspto-grants-1989_07
Patent number
US04851410

Reaction notes

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