Dimethylformamide → cis-8-fluoro-2-propyl-1,3,4,4a, 5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one

HRID 382814노트

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HRID 382814 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C@H:14]3[C@H:9]([CH2:10][CH2:11][NH:12][CH2:13]3)[CH2:8][C:7](=[O:15])[C:6]=2[CH:16]=1.Br[CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C@H:14]3[C@H:9]([CH2:10][CH2:11][N:12]([CH2:18][CH2:19][CH3:20])[CH2:13]3)[CH2:8][C:7](=[O:15])[C:6]=2[CH:16]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 86757545cis-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one

생성물 1

HCID 86757546cis-8-fluoro-2-propyl-1,3,4,4a, 5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one수율 63.8%

시약·촉매·용매 1

HCID 962Water용매

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온도
125 °C

실험 절차

A mixture of 0.29 g (1.32 mmol) of cis-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one, 0.12 ml (1.39 mmol) of bromopropane, 0.2 g (1.45 mmol) of potassium carbonate and 20 ml of anhydrous DMF was heated to 125° C. for 1 hour. Subsequently, the mixture was poured into 3 ml of water and extracted once with 50 ml of ethyl acetate. The organic phase was washed once with 40 ml of saturated sodium chloride solution, dried (MgSO4) and concentrated in a vacuum. The crude product obtained was purified by column chromatography on silica gel (methylene chloride/methanol/NH4OH 9:1:0.2). There were obtained 220 mg (63%) of cis-8-fluoro-2-propyl-1,3,4,4a, 5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one as a yellow oil, which was converted with MeOH/HCl into the hydrochloride with m.p. >220°.

후처리

  1. extractionextracted once with 50 ml of ethyl acetate
  2. washThe organic phase was washed once with 40 ml of saturated sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in a vacuum
  5. customThe crude product obtained
  6. customwas purified by column chromatography on silica gel (methylene chloride/methanol/NH4OH 9:1:0.2)

출처 및 근거

ORD 기록
ord-fe96d375b20c48fd8326b4dac1cd99aa
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310208B1

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