2,5-Dimethylpyrrolidine → HCID 15925277, 화합물

HRID 704186노트

반응식

HRID 704186 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

HCID 15925277HCID 15925277, 화합물수율 19.8%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4a7ee1bfb61941b794fb2f32d9eba35d
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04985419

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