Methyl iodide → 2,3-dihydro-2-methyl-7-methoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-pyrrolo[1,2-a]indol-1-one

HRID 22287노트

반응식

HRID 22287 반응식
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]3[CH2:12][CH:13]([CH2:16][CH:17]4[CH2:22][CH2:21][N:20]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:19][CH2:18]4)[C:14](=[O:15])[C:7]3=[CH:6][C:5]=2[CH:4]=1.[H-].[Na+].[CH3:32]I>C1COCC1>[CH3:32][C:13]1([CH2:16][CH:17]2[CH2:18][CH2:19][N:20]([CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:21][CH2:22]2)[CH2:12][N:8]2[C:9]3[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH:6]=[C:7]2[C:14]1=[O:15]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 538715712,3-dihydro-7-methoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-pyrrolo[1,2-a]indol-1-one

생성물 1

HCID 199278542,3-dihydro-2-methyl-7-methoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-pyrrolo[1,2-a]indol-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2,3-dihydro-7-methoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-pyrrolo[1,2-a]indol-1-one (137 mg, 0.353 mmol) in dry THF (5 ml) was treated with NaH (35 mg, 0.875 mmol) at r.t. After 5 minutes, an excess of methyl iodide (0.1 ml) was added and the mixture was stirred at r.t. for 3 hours. The mixture was quenched with water and extracted with chloroform. The organic layer was dried and concentrated to give 140 mg of material which was purified through silica gel to give the title compound. 1HNMR (CDCl3)δ 1.36 (s, 3H), 1.6-2.2 (m, 7H), 2.4-2.7 (m, 2H), 3.2-3.4 (m, 2H), 3.8 (s, 3H), 4.05 (s, 2H), 4.18 (ABq, 2H), 6.9 (s, 1H), 7.0-7.1 (m, 2H), 7.2-7.3 (m, 1H), 7.3-7.4 (m, 3H), 7.4-7.6 (m, 2H) ppm.

후처리

  1. customThe mixture was quenched with water
  2. extractionextracted with chloroform
  3. customThe organic layer was dried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5d4c8e44a481482486c8f0185c650681
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428043

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