Ethylamine hydrochloride → 2-(6-Bromo-3,4-dihydroquinolin-1(2H)-yl)-N-ethylethanamine

Temperatur

70 °C

A solution of 6-bromo-1-(2-iodoethyl)-1,2,3,4-tetrahydroquinoline (compound 3, 100 mg, 0.273 mmol) in acetonitrile (4.75 mL) and water (0.25 mL) in a 20 mL pressure vessel fitted with a stir-bar is treated with potassium carbonate (0.378 g, 2.73 mmol) and ethylamine hydrochloride (0.223 g, 2.73 mmol) and the sealed vessel stirred at 70° C. overnight. After 18 hours the mixture was partitioned between CH2Cl2 (50 mL) and water (10 mL) and transferred to a separatory funnel. The organic layer was separated and the aqueous layer extracted further with CH2Cl2. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give a yellow residue. The residue was purified on silica gel eluting with 7.5% 2M NH3 in methanol/92.5% dichloromethane to yield a yellow oil/residue, 4 (55 mg, 71.1%). 1H-NMR (CDCl3) δ 7.09 (dd, 1H, J=8.7, 2.4 Hz), 7.06-7.01 (m, 1H), 6.51 (d, 1H, J=8.7), 3.36 (t, 2H, J=6.8 Hz), 3.29 (t, 2H, J=5.5 Hz), 2.82 (t, 2H, J=6.8 Hz), 2.80-2.65 (2×m, 4H), 1.96-1.88 (m, 2H), 1.11 (t, 3H, J=7.1 Hz).

1. customAfter 18 hours the mixture was partitioned between CH2Cl2 (50 mL) and water (10 mL)
2. customtransferred to a separatory funnel
3. customThe organic layer was separated
4. extractionthe aqueous layer extracted further with CH2Cl2
5. washThe combined organic layer was washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customto give a yellow residue
10. customThe residue was purified on silica gel eluting with 7.5% 2M NH3 in methanol/92.5% dichloromethane

ORD-Eintrag

ord-3fd98828051f4f5eba924a8f54bba2dc

Quelldatensatz

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08173813B2