Dimethylamine → HCID 14726796, compound

HRID 1493284Notes

Reaction equation

HRID 1493284 reaction equation
Br[CH:2]([CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[CH:13]=[CH:14][CH:15]=[C:6]([C:7]=23)[S:5]1(=[O:17])=[O:16].[CH2:32]([N:34](CC)[CH2:35]C)C.CNC>C1(C)C=CC=CC=1>[CH3:32][N:34]([CH3:35])[CH:2]([CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[CH:13]=[CH:14][CH:15]=[C:6]([C:7]=23)[S:5]1(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 14726790HCID 14726790, compound

Product 1

HCID 14726796HCID 14726796, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-Bromo-3-[4-(4-fluorophenyl)-1-piperazinyl]propyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (4.2 g), triethylamine (1.1 cc) and dimethylamine (0.5 cc) in toluene (50 cc) are introduced into a 250 cc bomb ap paratus cooled to a temperature of about 0° C. The mixture is stirred and heated for 8 hours to a temperature close to 120° C., then cooled to a temperature of about 20° C. Stirring is continued for 15 hours at this temperature, then the reaction mixture is concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residual oil is purified by flash-chromatography on a silica column, under a current of argon at medium pressure (0.5-1.5 bar) with ethyl acetate as eluant. After recrystallization from boiling acetonitrile (15 cc), 2(2-dimethylamino-3-[4-(4-fluorophenyl)-1-piperazinyl]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (1.9 g) is obtained, m.p. 118° C. 2-(2-Bromo-3-[4-(4-fluorophenyl)-1-piperazinyl]propyl}naphtho[ 1,8-cd]isothiazole 1,1-dioxide may be prepared in the following manner: phosphorus tribromide (1 cc) is poured into 2-{3-[4-(4-fluorophenyl)-1-piperazinyl]-2-hydroxypropyl}naphtho[1,8-cd]isothiazole 1,1dioxide (11.5 g) in toluene (150 cc). The mixture is heated at boiling point for 4 hours, then is cooled to a temperature of about 20° C. The reaction mixture is redissolved in distilled water (300 cc) and alkalinized to pH 11 with N caustic soda (20 cc). The organic phase is extracted with dichloromethane (4×300 cc), dried centrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residual oil is purified by flash-chromatogra-phy on a silica column, under a current of argon at medium pressure (0.5-1.5 bar) with ethyl acetate as diluent. 2-(2-Bromo-3-[4-(4-fluorophenyl)-1-piperazinyl]pripyl}naptho[1,8j-cd]isothiazole 1,1-dioxide (5.7 g) is obtained, m.p. 102° C, which is used in the crude state in the subsequent syntheses.

Workup

  1. temperatureheated for 8 hours to a temperature
  2. customclose to 120° C.
  3. temperaturecooled to a temperature of about 20° C
  4. stirringStirring
  5. concentrationthe reaction mixture is concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  6. customThe residual oil is purified by flash-chromatography on a silica column
  7. customAfter recrystallization

Sources & evidence

ORD record
ord-b4157bcbbd244f49a7145acabee304ac
Source dataset
uspto-grants-1991_06
Patent number
US05021420

Reaction notes

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