Sodium Hydroxide → 2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-6-methyl-4-morpholin-4-yl-benzamide

Temperature

80 °C

To a solution of 2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide (0.26 g, 0.92 mmol) in benzene-tetrahydrofuran (1:1) (20 ml) are added tetrabutylammonium hydrogensulfate (0.031 g, 0.091 mmol) and 50% sodium hydroxide solution (8 ml) at RT. The reaction mixture is heated to 80° C. and 3-fluorobenzyl bromide (0.14 ml of a 2M solution in benzene, 0.28 mmol) is added. The reaction mixture is stirred at 80° C. for 15 min. After completion of the reaction (monitored by TLC), the reaction mixture is diluted with water (15 ml) and extracted with ethyl acetate (15×3 ml). The organic layer is washed with water (20 ml), brine (15 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 25% ethyl acetate/hexane) to yield 2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-6-methyl-4-morpholin-4-yl-benzamide (example 1) (0.06 g, 0.15 mmol, 16%). [M+H]+ 389.1.

1. customAfter completion of the reaction (monitored by TLC)
2. extractionextracted with ethyl acetate (15×3 ml)
3. washThe organic layer is washed with water (20 ml), brine (15 ml)
4. dry with materialdried over anhydrous sodium sulfate
5. customevaporated
6. customto get the crude product, which
7. customis purified by column chromatography (silica gel, 25% ethyl acetate/hexane)

ORD record

ord-feb3e339a00a4bd58b1d2ba57e451550

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108936B2