Oxalyl chloride → 4-cyclohexyl-N-hydroxy-N-methylcyclohexanecarboxamide

To a solution of 4-cyclohexyl-cyclohexanecarboxylic acid (1.47 g, 7 mmol) in 50 ml of tetrahydrofuran was added oxalyl chloride (0.67 ml, 7.7 mmol) and a few drops of dimethylformamide. After stirring for one hour, the reaction mixture was concentrated to about 1/3 of the original volume and added dropwise into a cold (~0° C.), stirred solution of N-methylhydroxylamine hydrochloride (1.17 g, 14 mmol) in 40 ml of 1N sodium hydroxide. The mixture was stirred for two hours and extracted three times with ethyl acetate. The combined ethyl acetate extracts were washed twice with water, dried with anhydrous sodium sulfate and concentrated. Purification by flash chromatography and crystallization afforded 0.342 g of 4-cyclohexyl-N-hydroxy-N-methylcyclohexanecarboxamide as a white solid (m.p. 89°-90° C.).

1. concentrationthe reaction mixture was concentrated to about 1/3 of the original volume
2. additionadded dropwise into a cold (~0° C.)
3. stirringThe mixture was stirred for two hours
4. extractionextracted three times with ethyl acetate
5. washThe combined ethyl acetate extracts were washed twice with water
6. dry with materialdried with anhydrous sodium sulfate
7. concentrationconcentrated
8. customPurification
9. customby flash chromatography and crystallization

ORD record

ord-19b7ee22410040a3bdf1d114a7a46b5d

Source dataset

uspto-grants-1989_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04889874