Pyrrolidine → HCID 14502142、化合物

HRID 728731ノート

反応式

HRID 728731 の反応式
CS(O[CH2:6][CH:7]([N:9]1[C:22]2[CH:21]=[C:20]([C:23]#[N:24])[CH:19]=[CH:18][C:17]=2[S:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH3:8])(=O)=O.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>C1(C)C=CC=CC=1>[N:25]1([CH2:6][CH:7]([N:9]2[C:22]3[CH:21]=[C:20]([C:23]#[N:24])[CH:19]=[CH:18][C:17]=3[S:16][C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH3:8])[CH2:29][CH2:28][CH2:27][CH2:26]1

参加物

4

反応物 2

HCID 31268PyrrolidineHCID 145021392-(2-Cyano-10-phenothiazinyl)propyl mesylate

生成物 1

HCID 14502142HCID 14502142、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of (2RS)-2-(2-cyano-l0-phenothiazinyl)-1-propyl methanesulphonate (10 g) and pyrrolidine (11.6 cc) in toluene (50 cc) is brought to 90° C. with stirring for 24 hours. After being cooled, the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. and the residue is taken up with ethyl ether (200 cc) and 4N aqueous sodium hydroxide solution (15 cc). After the mixture has been stirred for 10 minutes, settling is allowed to take place and the organic phase is washed with saturated aqueous sodium chloride solution (3×25 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 20° C. The residual oil (11.3 g) is dissolved in 0.5N aqueous hydrochloric acid solution (60 cc). This solution is washed with ethyl ether (100 cc) and then alkalinized with an excess of N aqueous sodium hydroxide solution and extracted with ethyl ether (100 cc). The organic phase is washed with saturated aqueous sodium chloride solution (50 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 20° C. The residual yellow oil (9.5 g) is purified on a column (height: 30 cm; diameter: 5.8 cm) of silica gel (0.04-0.063 mm) under a slight excess pressure of nitrogen (40 kPa), eluting with a mixture (95:5 by volume) (1 liter) of methylene chloride and methanol and collecting 100-cc fractions. Fractions 3 to 10 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-[(2RS)-l-(l-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonitrile (5.45 g) is thereby obtained in the form of a yellow oil.

後処理

  1. customis brought to 90° C.
  2. temperatureAfter being cooled
  3. concentrationthe mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  4. stirringAfter the mixture has been stirred for 10 minutes
  5. washthe organic phase is washed with saturated aqueous sodium chloride solution (3×25 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 20° C
  9. dissolutionThe residual oil (11.3 g) is dissolved in 0.5N aqueous hydrochloric acid solution (60 cc)
  10. washThis solution is washed with ethyl ether (100 cc)
  11. extractionextracted with ethyl ether (100 cc)
  12. washThe organic phase is washed with saturated aqueous sodium chloride solution (50 cc)
  13. dry with materialdried over magnesium sulphate
  14. filtrationfiltered
  15. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 20° C
  16. customThe residual yellow oil (9.5 g) is purified on a column (height: 30 cm; diameter: 5.8 cm) of silica gel (0.04-0.063 mm) under a slight excess pressure of nitrogen (40 kPa)
  17. washeluting with a mixture (95:5 by volume) (1 liter) of methylene chloride and methanol
  18. customcollecting 100-cc fractions
  19. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

出典と根拠

ORDレコード
ord-2192dfe65cff4140b4abbd74dc10cd38
出典データセット
uspto-grants-1991_09
特許番号
US05049669

反応ノート

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