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

Temperature

70 °C

To a solution of 2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide (synthesized according to the methods described in sections b) and c) of example 1) (0.20 g, 0.71 mmol) in benzene-tetrahydrofuran (1:1) (16 ml) are added tetrabutylammonium hydrogensulfate (0.024 g, 0.071 mmol) and 50% sodium hydroxide solution (6 ml) at RT. The reaction mixture is heated to 70° C. and 4-chlorobenzyl bromide (0.15 g, 0.71 mmol) is added. The reaction mixture is stirred at 70° C. for 20 min. After completion of the reaction (monitored by TLC), the organic layer is separated and the aqueous layer is extracted with ethyl acetate (2×20 ml). The organic layer is washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 28% ethyl acetate/hexane) to yield N-[(4-chlorophenyl)-methyl]-2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide (example 2) (0.095 g, 0.24 mmol, 50%). [M+H]+ 405.1.

1. customAfter completion of the reaction (monitored by TLC)
2. customthe organic layer is separated
3. extractionthe aqueous layer is extracted with ethyl acetate (2×20 ml)
4. washThe organic layer is washed with water (20 ml), brine (20 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. customevaporated
7. customto get the crude product, which
8. customis purified by column chromatography (silica gel, 28% ethyl acetate/hexane)

ORD record

ord-107606548ba64aac916d03a7c23b8180

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108936B2