Methylamine → HCID 70393690, compound

To a stirred solution of monomethylamine (50 ml, 1.13 mol) in 150 ml of methanol at 0° C. under nitrogen, was added 2-chloro-N-[(1,2-diphenyl-1-(trifluoromethyl)ethyl]acetamide (from Example 1) (10.2 g) followed by 100 ml of methanol to effect solution. The mixture was allowed to slowly warm to ambient temperature and stirred for 24 hours. The solvent was evaporated and the resulting semi-solid was dissolved in 150 ml of chloroform, 100 ml of water and 20 ml of 15% NaOH. The phases were separated, the aqueous phase extracted with chloroform (2×125 ml) and the combined organic phases washed with brine (150 ml), decolorized with charcoal, dried and evaporated to a yellow-orange oil, 9.8 g. This was dissolved in 150 ml of methanol, treated with 3.4 g of maleic acid and the solvent removed under vacuum to yield a solid which was recrystallized from methanol (150 ml) and ethyl acetate (150 ml), then from methanol (30 ml) and ethyl acetate (75 ml) and vacuum dried to give 4.88 g of 2-(methylamino)-N-[1,2-diphenyl-1-(trifluoromethyl)ethyl]acetamide maleate as a white solid, mp 179°-181° C.

1. customThe solvent was evaporated
2. dissolutionthe resulting semi-solid was dissolved in 150 ml of chloroform
3. customThe phases were separated
4. extractionthe aqueous phase extracted with chloroform (2×125 ml)
5. washthe combined organic phases washed with brine (150 ml)
6. customdried
7. customevaporated to a yellow-orange oil, 9.8 g
8. dissolutionThis was dissolved in 150 ml of methanol
9. additiontreated with 3.4 g of maleic acid
10. customthe solvent removed under vacuum
11. customto yield a solid which
12. customwas recrystallized from methanol (150 ml) and ethyl acetate (150 ml)
13. dry with materialfrom methanol (30 ml) and ethyl acetate (75 ml) and vacuum dried

ORD record

ord-aede2fbdb7894cf2b144e7e30f009c3c

Source dataset

uspto-grants-1989_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04798687