2-(azetidin-3-yl)quinoline dihydrochloride synthesis

2synthesis methods

Product Name:2-(azetidin-3-yl)quinoline dihydrochloride
CAS Number:1236861-65-6
Molecular formula:C12H12N2
Molecular Weight:184.24

tert-butyl 3-(quinolin-2-yl)azetidine-1-carboxylate

1236861-63-4
2 suppliers
inquiry

2-(azetidin-3-yl)quinoline dihydrochloride

1236861-65-6
10 suppliers
inquiry

Yield:1236861-65-6 48%

Reaction Conditions:

Stage #1: tert-butyl 3-(quinolin-2-yl)azetidine-1-carboxylatewith hydrogenchloride in methanol at 20; for 18 h;
Stage #2: with sodium hydroxide in water;

Steps:

7.1.C

A solution of C36 (1.0 g, 3.5 mmol) in methanolic hydrochloric acid (1.25M, 50 mL, 62 mmol) was stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo, and extracted with dichloromethane after conversion of product to the free base with 6N aqueous sodium hydroxide solution. Removal of solvent in vacuo provided C37. Yield: 310 mg, 1.68 mmol, 48%. LCMS m/z 185.2 (M+1). ¹H NMR (400 MHz, DMSO-d₆) δ 3.80 (dd, J=8.0, 8.0 Hz, 2H), 3.91 (dd, J=7.4, 7.4 Hz, 2H), 4.16 (m, 1H), 7.54 (d, J=8.3 Hz, 1H), 7.56 (ddd, J=8.1, 6.9, 1.1 Hz, 1H), 7.74 (ddd, J=8.4, 6.9, 1.6 Hz, 1H), 7.96 (m, 2H), 8.32 (d, J=8.5 Hz, 1H).

References:

US2010/190771,2010,A1 Location in patent:Page/Page column 21

2005-43-8 Synthesis

2005-43-8
205 suppliers
$6.00/250mg

1236861-65-6
10 suppliers
inquiry

References