Thionyl Chloride → 1-(4-Bromophenyl)-3-azabicyclo[3.1.0]hexane

To a solution of [2-aminomethyl-2-(4-bromo-phenyl)-cyclopropyl]-methanol (9.49 g, 37.02 mmol) in dichloroethane (120 mL), was added thionylchloride (3.2 mL, 44.4 mmol) at 0° C. and stirred for 2 h at r.t. After completion of the reaction as indicated by TLC, the reaction mixture was quenched with water (30 mL) at 0° C. Dichloroethane layer was separated from the acidic layer and discarded. The acidic layer was neutralized with sodium bicarbonate at 0° C. till pH=8 and extracted with 5% methanol in DCM (3×300 mL). The combined organic layers were dried over anhydrous sodium sulphate and concentrated to yield the title compound in crude form (5.20 g, 59%) as white gel, which was used as such in the next step.

1. customAfter completion of the reaction
2. customthe reaction mixture was quenched with water (30 mL) at 0° C
3. customDichloroethane layer was separated from the acidic layer
4. customwas neutralized with sodium bicarbonate at 0° C. till pH=8
5. extractionextracted with 5% methanol in DCM (3×300 mL)
6. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
7. concentrationconcentrated

ORD record

ord-f55ea9fed7d3432380abf35b81bee4ab

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906913B2