Sodium Iodide → HCID 13784678, compound

HRID 235631Notes

Reaction equation

Cl[CH2:2][CH2:3][CH:4]1[C:9](=[O:10])[N:8]([CH3:11])[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[S:5]1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[F:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH:4]3[C:9](=[O:10])[N:8]([CH3:11])[C:7]4[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=4[S:5]3)[CH2:25][CH2:24]2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 15 ml of dimethylformamide were added 1.21 g of 2-(2-chloroethyl)-4-methyl-2H-1,4-benzothiazin-3(4H)-one, 1.08 g of 1-(4-fluorophenyl)piperazine, 0.69 g of potassium carbonate and 0.05 g of sodium iodide. The mixture was stirred at 100° C. for 4 hours. The reaction solution was poured into ice-water and extracted with dichloromethane. The dichloromethane layer was washed with water and dried (MgSO4). Then, the solvent was evaporated off. The residue was subjected to a column chromatography on silica-gel (130 g). From the eluate with hexane-ethyl acetate (1:1, v/v) was obtained 2-[2-[4(4-fluorophenyl)-1-piperazinyl]ethyl]-4-methyl-2H-1,4-benzothiazin-3(4H)-one as an oily substance. This product was treated with methanol saturated with hydrogen chloride to give crystals of its hydrochloride. The yield was 0.99 g (43.2%). Recrystallization from methanol-ether gave prisms, m.p. 202°-204° C.

Workup

extractionextracted with dichloromethane
washThe dichloromethane layer was washed with water
dry with materialdried (MgSO4)
customThen, the solvent was evaporated off

Sources & evidence

ORD record: ord-42f751079ace4096bd322dfef973425a
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04640916

Reaction notes

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