Sodium Hydroxide → 5,6,7,8-Tetrahydroisoquinolin-1-amine

Temperature

170 °C

To a solution of 5,6,7,8-tetrahydroisoquinoline (5.0 g, 37.6 mmol) in DMF (8 mL) was added sodium amide (2.55 g, 63.9 mmol). The resulting mixture was heated to 170° C. for 16 h and cooled to room temperature. To the mixture was added aqueous 2 N NaOH (50 mL). The mixture was extracted with DCM (100 mL×3), and the combined organic phase was dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluting with DCM/MeOH v/v 10:1) to give 5,6,7,8-tetrahydroisoquinolin-1-amine as a yellow solid (2.6 g, yield 46%). ESI MS: m/z 149 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 7.80 (d, J=5.2 Hz, 1H), 6.44 (d, J=5.2 Hz, 1H), 4.34 (br, 2H), 2.67 (t, J=12 Hz, 2H), 2.39 (t, J=12 Hz, 2H), 1.88 (m, 2H), 1.78 (m, 2H).

1. temperaturecooled to room temperature
2. extractionThe mixture was extracted with DCM (100 mL×3)
3. dry with materialthe combined organic phase was dried over sodium sulfate
4. concentrationconcentrated
5. customThe residue was purified by silica gel column chromatography (
6. washeluting with DCM/MeOH v/v 10:1)

ORD record

ord-dff28ecfafe14c4abbfda4ef6765f976

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765760B2