Diethyl Ether → N-(4-aminocyclohexyl)methanesulfonamide

1,1-Dimethylethyl {4-[(methylsulfonyl)amino]cyclohexyl}carbamate (0.922 g, 3.15 mmol) was dissolved in DCM (50 mL). TFA was added (2.429 mL, 31.5 mmol) and the reaction allowed to stir at rt for 1 h. Evaporated off the volatiles and added DCM (50 mL) followed by evaporation of volatiles. The DCM addition/evaporation was repeated several times to give a maroon semi-solid. The residual semi-solid was treated with diethyl ether (10 mL) after which the suspension was sonicated and triturated, then filtered. Solids were triturated with more diethyl ether (10 mL). The product was suction dried to give title compound of Step B as a light pink solid (0.938 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.80 (br. s., 2H), 7.07 (d, J=7.2 Hz, 1H), 3.33 (s, 2H), 3.01-3.14 (m, 1H), 2.78-3.01 (m, 2H), 1.80-2.02 (m, 4H), 1.17-1.47 (m, 4H).

1. customEvaporated off the volatiles
2. additionadded DCM (50 mL)
3. customfollowed by evaporation of volatiles
4. customThe DCM addition/evaporation
5. customto give a maroon semi-solid
6. customwas sonicated
7. customtriturated
8. filtrationfiltered
9. customSolids were triturated with more diethyl ether (10 mL)
10. customThe product was suction dried

ORD-Eintrag

ord-66407a5bcb9c423a9c67ec3b454eee8b

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09233956B2