1-(1-Naphthyl)piperazine → 6-(2-(4-(1-Naphthyl)-piperazinyl)ethyl)benzothiazolone

HRID 1639275

반응식

HRID 1639275 반응식
Br[CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[CH:9][S:10](=[O:11])[C:6]=2[CH:5]=1.[C:14]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(CC(C)C)=O>[C:14]1([N:24]2[CH2:29][CH2:28][N:27]([CH2:2][CH2:3][C:4]3[CH:13]=[CH:12][C:7]4[N:8]=[CH:9][S:10](=[O:11])[C:6]=4[CH:5]=3)[CH2:26][CH2:25]2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 13421-(1-Naphthyl)piperazineHCID 10340Sodium CarbonateHCID 692279736-(2-Bromoethyl)benzothiazolone

생성물 1

HCID 692310686-(2-(4-(1-Naphthyl)-piperazinyl)ethyl)benzothiazolone

시약·촉매·용매 1

HCID 7909Methyl Isobutyl Ketone용매

실험 절차

To a 100 ml round-bottomed flask equipped with condenser and N2 inlet were added 1.0 g (3.88 mmol) of 6-(2-bromoethyl)benzothiazolone, 822 mg (3.88 mmol) N-(1-naphthyl)piperazine, 410 mg (3.88 mmol) sodium carbonate, and 50 ml methylisobutylketone. The reaction was refluxed for 24 hours, cooled, and was chromatographed on silica gel, eluting the byproducts with ethyl acetate (1 l) and the product with 4% methanol in ethyl acetate (1.5 l). The product fractions (Rf =0.2 in 5% methanol in ethyl acetate) were evaporated, taken up in methylene chloride, and precipitated by addition of ether saturated with HCl; the solid was filtered and washed with ether, dried, and washed with acetone. The latter was done by slurrying the solid with acetone and filtering. The title compound was obtained as a high melting, non-hygroscopic solid product, m.p. 288°-288.5° C., 0.78 g (59%).

후처리

  1. customTo a 100 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed for 24 hours
  3. temperaturecooled
  4. customwas chromatographed on silica gel
  5. washeluting the byproducts with ethyl acetate (1 l)
  6. customThe product fractions (Rf =0.2 in 5% methanol in ethyl acetate) were evaporated
  7. customprecipitated by addition of ether saturated with HCl
  8. filtrationthe solid was filtered
  9. washwashed with ether
  10. customdried
  11. washwashed with acetone
  12. filtrationfiltering

출처 및 근거

ORD 기록
ord-01f3e7c5fc6542e494a94dac6dbe930e
출처 데이터셋
uspto-grants-1989_11
특허 번호
US04883795

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