Hydrochloric Acid → 1-(9-Anthracenylsulfonyl)hexahydro-1H-1,4-Diazepine hydrochloride

HRID 1086448Notes

Reaction equation

[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[S:15]([Cl:18])(=[O:17])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[NH:26]1[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.Cl>C(Cl)Cl>[ClH:18].[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[S:15]([N:26]2[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)(=[O:17])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Add the product from step 2 (0.35 g, 1.28 mmol) in methylene chloride (20 mL) to a mixture of triethyl amine (0.605 mL, 4.34 mmol) and hexahydro-2H-1,4-diazepine (also known as homopiperazine) (0.326 g, 3.25 mmol) in methylene chloride (7 mL) cooled to 0° C. over 5 min. Stir the reaction mixture for 15 min at 0° C. Add aqueous HCl (25 mL, 1N) to the reaction mixture. Filter the solid and recrystallize from absolute ethanol to give the title compound (0.33 g, 69%) as light yellow needles. Rf=0.54 (5% MeOH in methylene chloride (v/v), 0.2% ammonium hydroxide buffer).

Workup

filtrationFilter the solid
customrecrystallize from absolute ethanol

Sources & evidence

ORD record: ord-c16a9c26bdaf48ae86fe7f572a5745b7
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05030631

Reaction notes

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