Water → HCID 13784665, compound

HRID 235632Notes

Reaction equation

HRID 235632 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH:17]3C=N[C:20]4[CH:23]=[CH:24][CH:25]=C[C:19]=4[S:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].CI.O.[CH3:32][N:33]([CH3:36])[CH:34]=[O:35]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][CH:17]3[C:34](=[O:35])[N:33]([CH3:36])[C:32]4[CH:25]=[CH:24][CH:23]=[CH:20][C:19]=4[S:18]3)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20220116HCID 20220116, compound

Product 1

HCID 13784665HCID 13784665, compound

Procedure

To a solution of 193 mg of 2-[3-[4-(4-fluorophenyl)-1-piperazinyl]propyl]-2H-1,4-benzothiazine in 2 ml of dimethylformamide was added 20 mg of 60% sodium hydride in oil. The mixture was stirred at room temperature for 30 minutes and cooled with ice. To the resultant was added 0.07 ml of methyl iodide, and the mixture was stirred for further one hour. The reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated to give 2-[3-[4-(4-fluorophenyl)-1-piperazinyl]propyl]-4-methyl-2H-1,4-benzothiazin-3(4H)-one as crystals. Recrystallization from ethyl acetate and hexane gave prisms, m.p. 103°-104° C. The yield was 84 mg (42%). IR and NMR spectra of this product was in agreement with those of the compound obtained in Example 34.

Workup

  1. temperaturecooled with ice
  2. stirringthe mixture was stirred for further one hour
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-17f8af16380148ecb6598323f9c607c7
Source dataset
uspto-grants-1987_02
Patent number
US04640916

Reaction notes

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