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

HRID 2294868Notes

Reaction equation

HRID 2294868 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.[CH3:19][C:20]1[CH:34]=[CH:33][C:23]2[O:24][CH:25]=[C:26]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[C:22]=2[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.C1(C)C=CC=CC=1.CN(C)C=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:30]3[CH2:31][CH2:32][CH:27]([C:26]4[C:22]5[CH:21]=[C:20]([CH3:19])[CH:34]=[CH:33][C:23]=5[O:24][CH:25]=4)[CH2:28][CH2:29]3)[S:12][C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 214720324-(5-Methylbenzo(b)furan-3-yl)piperidine hydrochlorideHCID 214720436-Acetyl-2-(2-chloroethyl)-3-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Product 1

HCID 214719816-Acetyl-3-ethyl-2-(2-(4-(5-methylbenzo(b)-furan-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5.0 g of 6-acetyl-2-(2-chloroethyl)-3-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine, 4.9 g of 4-(5-methylbenzo(b)furan-3-yl)piperidine hydrochloride, 2.5 g of potassium carbonate, 3.0 g of potassium iodide, 30 ml of dimethylformamide and 30 ml of toluene was stirred at 70° C. for 7 hours and then poured into water. The toluene layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on a silica gel and then dissolved into ethanol to make a hydrochloride. The resulting crystals were recrystallized from isopropyl alcohol to give 6-acetyl-3-ethyl-2-(2-(4-(5-methylbenzo(b)-furan-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride, m.p. 222°-225° C.

Workup

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

Sources & evidence

ORD record
ord-63bd3c7587e041daa193bfd02dde640e
Source dataset
uspto-grants-1997_11
Patent number
US05691330

Reaction notes

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