반응 #4947

반응 방정식

fumaric acid

2-methylpyrrolidine

2-(chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione

potassium carbonate

→

yellow crystals

수율 32.8%

2,3-Dihydro-4-methyl-2-[2-(2-methyl-1-pyrrolidinyl)ethyl]pyrido[3,2-f][1,4]oxazepine-5(4H)-thione fumarate compound with 2-propanol

수율 32.8%

용매

ethanol

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도to reflux for 6.5 hr
3. 3
   workup.WAITleft
4. 4
   온도heating
5. 5
   온도at reflux
6. 6
   workup.WAITwas continued for 24 hr
7. 7
   기타Ethanol was removed by rotary evaporation (70° C., 30 mm)
8. 8
   세척washed with 2×50 ml dil. aqueous sodium hydroxide
9. 9
   건조The organic layer was dried over anhydrous sodium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated by rotary evaporation (70° C., 30 mm)
12. 12
    workup.DISSOLUTIONThe residual syrup was dissolved in isopropyl aocohol
13. 13
    기타Two recrystallizations from isopropyl

실험 절차

To a suspension of 5.0 g (0.019 mole) of 2-(chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione in 25 ml of absolute ethanol was added 3.5 g (0.04 mole) of 2-methylpyrrolidine. The mixture was heated to reflux for 6.5 hr and left standing at room temperature overnight. Mass spec and TLC showed presence of starting materials. Approximately 5 g of potassium carbonate was added and heating at reflux was continued for 24 hr. Ethanol was removed by rotary evaporation (70° C., 30 mm). The residue was taken up in 100 ml of methylene chloride and washed with 2×50 ml dil. aqueous sodium hydroxide. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation (70° C., 30 mm). The residual syrup was dissolved in isopropyl aocohol and treated with fumaric acid affording 4.5 g (0.01 mole, 49.2%) of crude crystals. Two recrystallizations from isopropyl afforded 1.5 g (16.4%) of yellow crystals, m.p., 92°-95° C.

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