Potassium Iodide → HCID 21471795, compound

HRID 1734093Notes

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.[Cl:19][C:20]1[C:28]2[C:27]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[CH:26][O:25][C:24]=2[CH:23]=[C:22]([Cl:35])[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:32]3[CH2:33][CH2:34][CH:29]([C:27]4[C:28]5[C:20]([Cl:19])=[CH:21][C:22]([Cl:35])=[CH:23][C:24]=5[O:25][CH:26]=4)[CH2:30][CH2:31]3)[S:12][C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 0.9 g of 6-acetyl-2-(2-chloroethyl)-3-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine, 1.0 g of 4-(4,6-dichlorobenzo(b)furan-3-yl)piperidine hydrochloride, 0.5 g of potassium carbonate, 0.5 g of potassium iodide, 25 ml of dimethylformamide and 25 ml of toluene was stirred at 80° C. for 6 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-2-(2-(4-(4,6-dichlorobenzo(b)furan-3-yl)piperidin-1-yl)ethyl)-3-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride, m.p. 260° C. (decomposition).

Workup

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

Sources & evidence

ORD record: ord-8218c7141d4a40349f7d41a741f4afe7
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05532240

Reaction notes

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