Triethylamine → HCID 14726799, compound

HRID 1493285Notes

Reaction equation

HRID 1493285 reaction equation
Br[CH2:2][CH2:3][CH:4]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[CH:15]=[CH:16][CH:17]=[C:8]([C:9]=23)[S:7]1(=[O:19])=[O:18])[CH3:5].C(N(CC)CC)C.[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[F:27][C:28]1[CH:29]=[CH:30][C:31]([N:34]2[CH2:39][CH2:38][N:37]([CH2:2][CH2:3][CH:4]([N:6]3[C:10]4[CH:11]=[CH:12][CH:13]=[C:14]5[CH:15]=[CH:16][CH:17]=[C:8]([C:9]=45)[S:7]3(=[O:19])=[O:18])[CH3:5])[CH2:36][CH2:35]2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752601-(4-Fluorophenyl)piperazineHCID 14726793HCID 14726793, compound

Product 1

HCID 14726799HCID 14726799, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

The experiment is carried out as in Example 56, starting with 2-(4-bromo-2-butyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (5.2 g), triethylamine (2.1 cc) and 4-(4-fluorophenyl)piperazine (2.8 g) in toluene (200 cc). The mixture is heated at boiling point for 8 hours and then cooled to a temperature of about 20° C. After purification by flash-chromatography on a silica column, under a current of argon at medium pressure (0.5-1.5 bar) with a mixture of dichloromethane and ethyl acetate (90-10 as eluant, crystallization from isopropyl oxide (30 cc) and recrystallization from boiling acetonitrile (10 cc), 2-{4-[4-(4-fluorophenyl)-1-piperazinyl]-2butyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (1.2 g) is obtained, m.p. 116° C.

Workup

  1. temperatureThe mixture is heated
  2. customfor 8 hours
  3. customAfter purification by flash-chromatography on a silica column
  4. additionunder a current of argon at medium pressure (0.5-1.5 bar) with a mixture of dichloromethane and ethyl acetate (90-10 as eluant
  5. customcrystallization
  6. customfrom isopropyl oxide (30 cc) and recrystallization

Sources & evidence

ORD record
ord-6341e94c1ebe4ec2b0f02027b8f3db44
Source dataset
uspto-grants-1991_06
Patent number
US05021420

Reaction notes

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