Acetic Anhydride → 1,2,3,4-Tetrahydro-2-[[1-(phenylmethyl)-4-piperidinyl]methylene]cyclopent[b]indol-1-one

온도

-78 °C

To a mixture of 1,2,3,4-tetrahydrocyclopent[b]-indol-1-one (440 mg, 2.6 mmol) and 1-benzylpiperidine-4-carboxaldehyde (581 mg, 2.86 mmol) in 90 ml dry THF was added 5.4 mmol of lithium diisopropylamide at -78° C. The mixture was stirred at -78° C. for 30 minutes, then warmed up to 0° C. for 1.5 hours, and then to r.t. for 15 minutes. Acetic anhydride (0.265 g, 2.6 mmol) was added, the mixture was stirred at r.t. for 1.5 hours and quenched ammonium chloride, water and extracted with chloroform. The organic layer was dried, concentrated, and purified through silica gel to give the title compound. 1HNMR (CDCl3)δ 1.45-1.7 (m, 3H), 1.8-2.3 (m, 4H), 2.8-3.0 (m, 2H), 3.46 (s, 2H), 3.55 (s, 2H), 6.5 (m, 1H), 7.1-7.4 (m, 8H), 7.9 (m, 1H), 9.2 (s, 1H) ppm.

1. temperaturewarmed up to 0° C. for 1.5 hours
2. waitto r.t. for 15 minutes
3. stirringthe mixture was stirred at r.t. for 1.5 hours
4. customquenched ammonium chloride, water
5. extractionextracted with chloroform
6. customThe organic layer was dried
7. concentrationconcentrated
8. custompurified through silica gel

ORD 기록

ord-38dbbafc6f744e7f8c4c06aaaa9e7d7c

출처 데이터셋

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05428043