Water → 6-Benzoyl-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 2294816Notes

Reaction equation

HRID 2294816 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]4[C:25]5[CH2:24][CH2:23][NH:22][CH2:21][C:20]=5[S:19][C:18]=4[CH3:26])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>C(N(CC)CC)C.C(Cl)(Cl)Cl>[C:29]([N:22]1[CH2:23][CH2:24][C:25]2[C:17]([CH2:16][CH2:15][N:12]3[CH2:13][CH2:14][CH:9]([C:6]4[C:5]5[CH:27]=[CH:28][C:2]([F:1])=[CH:3][C:4]=5[O:8][N:7]=4)[CH2:10][CH2:11]3)=[C:18]([CH3:26])[S:19][C:20]=2[CH2:21]1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 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

Product 1

HCID 214719626-Benzoyl-3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridineYield 63.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 0.5 g of 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 0.5 ml of triethylamine and 10 ml of chloroform was added 0.18 g of benzoyl chloride under cooling and the mixture was stirred for an hour, and then poured into water. The organic layer was washed with water, dried and concentrated. The residue was purified by column chlomatogaphy to give 0.4 g of 6-benzoyl-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 as an oil, m.p. 192°-195° C. as oxalate 1/4hydrate thereof.

Workup

  1. temperatureunder cooling
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chlomatogaphy

Sources & evidence

ORD record
ord-87475abca1ed4cf3847e37936cbeb5b4
Source dataset
uspto-grants-1997_11
Patent number
US05691330

Reaction notes

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