Potassium Iodide → 6-Acetyl-3-ethyl-2-(2-(4-(6-fluorobenzo(b)furan-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine hydrochloride

HRID 2294866Notes

Reaction equation

HRID 2294866 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[C:10]([CH2:16][CH3:17])=[C:11]([CH2:13][CH2:14][Cl:15])[S:12][C:6]=2[CH2:5]1)(=[O:3])[CH3:2].Cl.[F:19][C:20]1[CH:21]=[CH:22][C:23]2[C:27]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:26][O:25][C:24]=2[CH:34]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.C1(C)C=CC=CC=1.O>[ClH:15].[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[C:10]([CH2:16][CH3:17])=[C:11]([CH2:13][CH2:14][N:31]3[CH2:32][CH2:33][CH:28]([C:27]4[C:23]5[CH:22]=[CH:21][C:20]([F:19])=[CH:34][C:24]=5[O:25][CH:26]=4)[CH2:29][CH2:30]3)[S:12][C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 214720436-Acetyl-2-(2-chloroethyl)-3-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridineHCID 226493394-(6-Fluorobenzofuran-3-yl)piperidine hydrochloride

Product 1

HCID 214717926-Acetyl-3-ethyl-2-(2-(4-(6-fluorobenzo(b)furan-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine hydrochlorideYield 27.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.0 g of 6-acetyl-2-(2-chloroethyl)-3-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine, 0.95 g of 4-(6-fluorobenzo(b)furan-3-yl)piperidine hydrochloride, 3.0 g of potassium carbonate and 1.0 g of potassium iodide in 25 ml of dimethylformamide and 25 ml of toluene was stirred at 70° C. for 7 hours and poured into water. The toluene layer was washed with water, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on a silica gel and dissolved in ethanol to convert hydrochloride thereof, and then recrystallized from isopropyl alcohol to give 0.5 g of 6-acetyl-3-ethyl-2-(2-(4-(6-fluorobenzo(b)furan-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine hydrochloride, m.p. 205° C. (decomposition).

Workup

  1. washThe toluene layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on a silica gel
  5. dissolutiondissolved in ethanol
  6. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-8587f345668b41b39c87afeb89697ff7
Source dataset
uspto-grants-1997_11
Patent number
US05691330

Reaction notes

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