1,4-Dioxane → 3-[1-(3-chloro-4-methyl-2-thienyl)cyclopentyl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine

HRID 502977Notes

Reaction equation

CO[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]=1.O1CCOCC1.[Cl:16][C:17]1[C:21]([CH3:22])=[CH:20][S:19][C:18]=1[C:23]1([C:28]([NH:30][NH2:31])=O)[CH2:27][CH2:26][CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[Cl:16][C:17]1[C:21]([CH3:22])=[CH:20][S:19][C:18]=1[C:23]1([C:28]2[N:9]3[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]3=[N:31][N:30]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 100 °C

Procedure

7-Methoxy-3,4,5,6-tetrahydro-2H-azepine (0.5 ml) was added to a dioxane (20 ml) and toluene (15 ml) solution of 1-(3-chloro-4-methyl-2-thienyl)cyclopentane-carbohydrazide (800 mg), followed by stirring at 100° C. for 3 days. The reaction solution was subjected to evaporation under reduced pressure and the resulting crude product was purified by column chromatography (chloroform:methanol=40:1). The resulting solid was washed with hexane to obtain 770 mg of 3-[1-(3-chloro-4-methyl-2-thienyl)cyclopentyl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine (colorless solid).

Workup

customThe reaction solution was subjected to evaporation under reduced pressure
customthe resulting crude product was purified by column chromatography (chloroform:methanol=40:1)
washThe resulting solid was washed with hexane

Sources & evidence

ORD record: ord-1b22d66d9ac046ea9d02b66f5e6d3278
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776897B2

Reaction notes

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