1-Boc-hexahydro-1,4-diazepine

Chemical properties

Colorless to yellow liquid

The Uses of 1-Boc-hexahydro-1,4-diazepine

1-Boc-hexahydro-1,4-diazepine is a diazepine derivative used in the preparation of pharmaceutical compounds such as histamine H3-receptor antagonists and dipeptidyl peptidase IV (DPP-IV) inhibitors.

The Uses of 1-Boc-hexahydro-1,4-diazepine

1-Boc-homopiperazine is used in synthesis of potent anticoagulant. It is also used to produce 4-(7,8,9,10-tetrahydro-6H-cyclohepta[b]quinolin-11-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester by reaction with 11-bromo-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinoline.

General Description

1-Boc-hexahydro-1,4-diazepine is an N-boc protected homopiperazine. Its enthalpy of vaporization at boiling point (558.15K) is 49.498kjoule/mol.

Synthesis

To a solution of di-tert-butyldicarbonate (2.201 g, 9.780 mmol) in acetic acid (9.8 mL), a solution of 1,4-diazepane (1.0 g, 9.780 mmol) in acetic acid (9.8 mL) is added at room temperature. After 24 hours, water is added and the pH is adjusted to 10 using 10% NaOH. The aqueous phase is then extracted with dichloromethane (2 x 15 mL). The organic phase is dried and the solvent is evaporated to obtain tert-butyl 1,4-diazepane-1-carboxylate (1-Boc-hexahydro-1,4-diazepine) with a yield of 90.0%.

Precautions

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store under inert gas. It is sensitive to air.

References

Synthesis and biological activity of novel 1,4-diazepane derivatives as factor Xa inhibitor with potent anticoagulant and antithrombotic activity. Bioorganic &Medicinal Chemistry. 2004, 12 (9), 2179-2191.
Discovery and structure-activity relationship of thienopyridine derivatives as bone anabolic agents. Bioorganic & medicinal chemistry. 2013, 21 (7), 1628-1642.