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

HRID 1639275

反応式

HRID 1639275 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7909Methyl Isobutyl Ketone溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-01f3e7c5fc6542e494a94dac6dbe930e
出典データセット
uspto-grants-1989_11
特許番号
US04883795

関連ノート

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