Acetic Anhydride → HCID 54082237, 화합물

HRID 22288

반응식

HRID 22288 반응식
[C:1]1(=[O:13])[C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[NH:5][C:4]=2[CH2:3][CH2:2]1.[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([CH:27]=O)[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([N-]C(C)C)(C)C.[Li+].C(OC(=O)C)(=O)C>C1COCC1>[C:15]1([CH2:14][N:21]2[CH2:26][CH2:25][CH:24]([CH:27]=[C:2]3[CH2:3][C:4]4[NH:5][C:6]5[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=5[C:12]=4[C:1]3=[O:13])[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 7918Acetic AnhydrideHCID 895841-Benzylpiperidine-4-carbaldehydeHCID 2724682Lithium diisopropylamideHCID 64246693,4-Dihydrocyclopenta(b)indol-1(2H)-one

생성물 1

HCID 54082237HCID 54082237, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-38dbbafc6f744e7f8c4c06aaaa9e7d7c
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428043

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