2,5-Dimethylpyrrolidine → HCID 15925277、化合物

HRID 704186ノート

反応式

HRID 704186 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.[CH3:25][CH:26]1[CH2:30][CH2:29][CH:28]([CH3:31])[NH:27]1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:25][CH:26]1[CH2:30][CH2:29][CH:28]([CH3:31])[N:27]1[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]

参加物

5

反応物 2

HCID 960342,5-DimethylpyrrolidineHCID 145021392-(2-Cyano-10-phenothiazinyl)propyl mesylate

生成物 1

HCID 15925277HCID 15925277、化合物収率 19.8%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2-(2-cyano-10-phenothiazinyl)-1-propyl methanesulphonate (5 g) and (2RS,5RS)-2,5-dimethylpyrrolidine (5 g) in toluene (50 cc) is heated for 4 days to a temperature in the region of 100° C. After cooling, the reaction mixture is diluted with ethyl acetate (200 cc) and extracted successively with N aqueous hydrochloric acid solution (50 cc and 2×25 cc). The combined aqueous phases are alkalinized with 10N aqueous sodium hydroxide solution to pH 13, and extracted successively with ethyl ether (200 cc and 50 cc). The combined organic phases are dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. The residual yellow gum (2.8 g) is purified by chromatography on a column (height: 30 cm; diameter: 2 cm) of silica gel (0.2-0.063 mm), eluting with a mixture (80:20 by volume) (500 cc) of cyclohexane and ethyl acetate and collecting 30-cc fractions. The combined fractions 5 to 11 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The viscous yellow residue (2.4 g) is dissolved in isopropyl ether (15 cc) under reflux. The solution is cooled and then kept for 2 hours at a temperature in the region of 5° C. The crystals formed are drained, washed with isopropyl ether (2 cc) and dried under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C. 10-((2RS)-1-[(2RS,5RS)-2,5-dimethyl-1-pyrrolidinyl]-2-propyl}-2-phenothiazine carbonitrile (1 g) is thereby obtained in the form of pale yellow crystals, m.p. 105° C.

後処理

  1. temperatureAfter cooling
  2. extractionextracted successively with N aqueous hydrochloric acid solution (50 cc and 2×25 cc)
  3. extractionextracted successively with ethyl ether (200 cc and 50 cc)
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C
  7. customThe residual yellow gum (2.8 g) is purified by chromatography on a column (height: 30 cm; diameter: 2 cm) of silica gel (0.2-0.063 mm)
  8. washeluting with a mixture (80:20 by volume) (500 cc) of cyclohexane and ethyl acetate
  9. customcollecting 30-cc fractions
  10. concentrationThe combined fractions 5 to 11 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  11. dissolutionThe viscous yellow residue (2.4 g) is dissolved in isopropyl ether (15 cc)
  12. temperatureunder reflux
  13. temperatureThe solution is cooled
  14. customThe crystals formed
  15. washwashed with isopropyl ether (2 cc)
  16. customdried under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C

出典と根拠

ORDレコード
ord-4a7ee1bfb61941b794fb2f32d9eba35d
出典データセット
uspto-grants-1991_01
特許番号
US04985419

反応ノート

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