1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86621468, compound

HRID 1711593Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:11][C@H:10]2N)=[CH:5][CH:4]=1.[N:13]12CCCN=C1CCCCC2.[CH:24]([S:27](Cl)(=[O:29])=[O:28])([CH3:26])[CH3:25]>ClCCl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:11][CH:10]2[CH2:25][CH:24]([S:27]([NH2:13])(=[O:29])=[O:28])[CH3:26])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Trans-2-(4-chlorophenyl)cyclopropanamine hydrochloride (see Bioorganic and Medical Chemistry 12(9), 2021-2034, 2004) (628 mg, 3.08 mmol) was suspended in dry dichloromethane (15 ml) and cooled to 0° C. with stirring under argon. 1,8-Diazabicyclo[5.4.0]undec-7-ene (1.40 g, 9.225 mmol) was added, followed by the dropwise addition of isopropylsulfonyl chloride (877 mg, 6.15 mmol) with stirring under an atmosphere of argon. The reaction mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was then washed with 1 N HCl (2×50 ml). The organic layer was dried over sodium sulphate and evaporated in vacuo to give a yellow oil. The crude product was chromatographed on a 5 g isolute silica Sep-Pak® column eluting from 0-50% ethyl acetate in petroleum ether to give the title compound (570 mg, 68%); mass spectrum (API−): Found 272 (MH−);

Workup

stirringwith stirring under an atmosphere of argon
temperatureto warm to room temperature
stirringstirred for 1 h
washThe reaction mixture was then washed with 1 N HCl (2×50 ml)
dry with materialThe organic layer was dried over sodium sulphate
customevaporated in vacuo
customto give a yellow oil
customThe crude product was chromatographed on a 5 g isolute silica Sep-Pak® column
washeluting from 0-50% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-47ad073884744b4bb5c0b194344655c8
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790758B2

Reaction notes

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