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

HRID 979307Notes

Reaction equation

[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

Participants

Conditions

Temperature: 100 °C

Procedure

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°.

Workup

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

Sources & evidence

ORD record: ord-e81ef2a457754b34b5356785c2314928
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04667032

Reaction notes

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