1-(6-Bromo-3-pyridyl)homopiperazine synthesis

5synthesis methods

Product Name:1-(6-Bromo-3-pyridyl)homopiperazine
CAS Number:223797-21-5
Molecular formula:C10H14BrN3
Molecular Weight:0

tert-Butyl 4-(6-bromopyridin-3-yl)-1,4-diazepane-1-carboxylate

223797-58-8
4 suppliers
inquiry

223797-21-5
8 suppliers
inquiry

Yield:223797-21-5 64%

Reaction Conditions:

with trifluoroacetic acid in dichloromethane at 20; for 16 h;

Steps:

24 3.2.24. 1-(6-Bromopyridin-3-yl)-4-(3-phenylpropyl)-1,4-diazepane (28)

A solution of 58 (598 mg, 1.68 mmol) and TFA (2.58 mL, 33.7 mmol) in DCM (20 mL) was stirred at rt for 16 h.
The reaction mixture was evaporated in vacuo.
The residue was added aq NaOH solution (4 M, 20 mL) and extracted with DCM (3 * 100 mL).
The combined organic phases were dried (MgSO₄), filtered, and evaporated in vacuo giving 1-(6-bromopyridin-3-yl)-1,4-diazepane as a yellow oil (274 mg, 64%) that crystallizes over time. ¹H NMR (CDCl₃, 400 MHz) δ 7.84 (d, 1H, J = 3.3 Hz), 7.23 (dd, 1H, J = 8.8, 0.5 Hz), 6.86 (dd, 1H, J = 8.9, 3.4 Hz), 3.54 (dt, 4H, J = 16.7, 5.8 Hz), 3.08-3.00 (m, 2H), 2.89-2.80 (m, 2H), 2.28 (bs, 1H), 1.97-1.85 (m, 2H).
¹³C NMR (CDCl₃, 101 MHz) δ 143.90, 133.91, 127.59, 126.76, 121.08, 51.71, 47.95, 47.91, 47.89, 28.92.

References:

Bach, Tinna B.;Jensen, Anders A.;Petersen, Jette G.;S?rensen, Troels E.;Della Volpe, Serena;Liu, Jun;Blaazer, Antoni R.;Van Muijlwijk-Koezen, Jacqueline E.;Balle, Thomas;Fr?lund, Bente [European Journal of Medicinal Chemistry,2015,vol. 102,art. no. 8008,p. 425 - 444]

223796-20-1 Synthesis