Ethyl Acetate → 7-Methoxy-2-(4-methylpiperazin-1-yl)-3H-phenothiazine-3-one

HRID 979307ノート

反応式

HRID 979307 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]1[C:7](=[CH:8][C:9](=[O:17])[CH:10]=[CH:11]1)[S:6]2.Cl.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(OCC)(=O)C>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]1[C:7](=[CH:8][C:9](=[O:17])[C:10]([N:23]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)=[CH:11]1)[S:6]2

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 121968951-Methylpiperazine hydrochlorideHCID 137248777-methoxy-3H-phenothiazin-3-one

生成物 1

HCID 138537347-Methoxy-2-(4-methylpiperazin-1-yl)-3H-phenothiazine-3-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 7-methoxy-3H-phenothiazin-3-one (1.2 g) and N-methyl piperazine HCl (3.4 g) in DMF (20 ml) was heated at 100° C. for 3 hours. Then NaIO4 (1 g) was added and the reaction mixture was heated at 100° C. for 1 hour. Ice-water was added to the reaction mixture followed by ethyl acetate. The aqueous layer was decanted, filtered and the filtrate basified with K2CO3 and extracted with ethyl acetate. The organic layer was evaporated to dryness, the resulting residue was dissolved in CH2Cl2, dried and evaporated to dryness to afford the crude final product (1.2 g) which was purified by chromatography on silica gel column eluting with 10% MEOH/CH2Cl2 to give the title compound, m.p. 208°-209°.

後処理

  1. temperaturethe reaction mixture was heated at 100° C. for 1 hour
  2. customThe aqueous layer was decanted
  3. filtrationfiltered
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was evaporated to dryness
  6. dissolutionthe resulting residue was dissolved in CH2Cl2
  7. customdried
  8. customevaporated to dryness
  9. customto afford the crude final product (1.2 g) which
  10. customwas purified by chromatography on silica gel column
  11. washeluting with 10% MEOH/CH2Cl2

出典と根拠

ORDレコード
ord-e81ef2a457754b34b5356785c2314928
出典データセット
uspto-grants-1987_05
特許番号
US04667032

反応ノート

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