Isopropylamine → HCID 60754457, compound

Temperature

0 °C

To a solution of 3-bromomethyl-benzonitrile (2 g, 10.2 mmol) in EtOH (50 mL) is added a solution of Na2SO3 (1.3 g, 10.3 mmol) in H2O (50 mL) and the mixture is heated at reflux for 4 hours. The mixture is concentrated in vacuo. The residue is suspended in DCM (100 mL) and DMF (1 mL), cooled to 0° C. and treated with oxalyl chloride (4.5 mL, 24.4 mmol). The mixture is warmed to room temperature for 3 hours. The mixture is diluted with brine (100 mL), extracted with DCM (2×100 mL), dried with Na2SO4, filtered, and concentrated in vacuo. The residue is dissolved in THF (100 mL), and treated with isopropyl amine (3.5 mL, 40.8 mmol). The mixture is stirred for 12 h, diluted with EtOAc (200 mL), washed with saturated aqueous NH4Cl (2×100 mL), dried with Na2SO4, filtered, and concentrated in vacuo. The residue is purified by flash chromatography eluting with 20%-80% EtOAc/heptane to afford C-(3-cyano-phenyl)-N-isopropyl-methanesulfonamide as a powder. MS: 237 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 1.10 (d, J=6.6 Hz, 6H), 3.36 (m, 1H), 4.42 (s, 2H), 7.09 (m, 1H), 7.57 (m, 1H), 7.74 (m, 1H), 7.85 (m, 2H).

1. temperaturethe mixture is heated
2. temperatureat reflux for 4 hours
3. concentrationThe mixture is concentrated in vacuo
4. temperatureThe mixture is warmed to room temperature for 3 hours
5. extractionextracted with DCM (2×100 mL)
6. dry with materialdried with Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. dissolutionThe residue is dissolved in THF (100 mL)
10. washwashed with saturated aqueous NH4Cl (2×100 mL)
11. dry with materialdried with Na2SO4
12. filtrationfiltered
13. concentrationconcentrated in vacuo
14. customThe residue is purified by flash chromatography
15. washeluting with 20%-80% EtOAc/heptane

ORD record

ord-9d393fa9fddb4fe69933fbcd08a3dbc5

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202863B2