6-Acetyl-3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl) ethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine → 3-(2-(4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine

HRID 1734044

Reaction equation

HRID 1734044 reaction equation
C([N:4]1[CH2:9][CH2:8][C:7]2[C:10]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH:19]([C:22]4[C:26]5[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:25]=5[O:24][N:23]=4)[CH2:18][CH2:17]3)=[C:11]([CH3:13])[S:12][C:6]=2[CH2:5]1)(=O)C>S(=O)(=O)(O)O.O>[F:31][C:29]1[CH:28]=[CH:27][C:26]2[C:22]([CH:19]3[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][C:10]4[C:7]5[CH2:8][CH2:9][NH:4][CH2:5][C:6]=5[S:12][C:11]=4[CH3:13])[CH2:17][CH2:18]3)=[N:23][O:24][C:25]=2[CH:30]=1

Participants

4

Reactant 1

HCID 214719256-Acetyl-3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl) ethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine

Product 1

HCID 214719903-(2-(4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 4 g of 6-acetyl-3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine in 4 ml of conc. sulfuric acid and 80 ml of water was refluxed under heating for 3 hours. The mixture was poured into water, made alkaline and extracted with chloroform. The organic layer was washed with water, dried over magnesium sulfate and concentrated. To the residue was added isopropyl ether and the crystals were collected by filtration to give 3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine, m.p. 88°-90° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 3 hours
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. additionTo the residue was added isopropyl ether
  8. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-09a168a13d3e43bc8b6e8c9883a7aceb
Source dataset
uspto-grants-1996_07
Patent number
US05532240

Linked notes

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