Toluene → HCID 19830852, compound

HRID 1493263Notes

Reaction equation

HRID 1493263 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[CH:14]=[CH:15][CH:16]=[C:7]([C:8]=23)[S:6]1(=[O:18])=[O:17].[CH2:19]([N:21](CC)CC)[CH3:20].[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)=[C:34]2CCNC[CH2:35]2)=[CH:29][CH:28]=1.[I-].[Na+].[C:49]1(C)C=CC=CC=1>>[F:46][C:43]1[CH:44]=[CH:45][C:40]([C:33]2([C:30]3[CH:29]=[CH:28][C:27]([F:26])=[CH:32][CH:31]=3)[CH2:34][C:35](=[CH2:49])[CH2:20][CH2:19][N:21]2[CH2:2][CH2:3][CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[CH:14]=[CH:15][CH:16]=[C:7]([C:8]=34)[S:6]2(=[O:18])=[O:17])=[CH:41][CH:42]=1

Participants

6

Reactant 5

HCID 1140TolueneHCID 5238Sodium IodideHCID 8471TriethylamineHCID 27244364-(Bis(4-fluorophenyl)methylene)piperidineHCID 145800262(3-Chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide

Product 1

HCID 19830852HCID 19830852, compound

Conditions

Temperature
20 °C

Procedure

The experiment is carried out as in Example 1, starting with 2-(3-chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (3.9 g), triethylamine (1.9 cc), 4-[bis(4-fluorophenyl)methylene]piperidine (3.7 g) and sodium iodide (2.1 g) in toluene (150 cc). The mixture is heated for 6 hours at boiling point, then cooled to a temperature of about 20° C. After purification by flashchromatography on a silica column., under a current of argon at medium pressure (0.5-1.5 bar) with dichloromethene as eluant, 2-(3-[bis(4-fluorophenyl)-4-methylenepiperidino]propyl}naphtho[1,8-cd]-isothiazole 1,1-dioxide (4.6 g) is obtained in the form of a brown oil which is converted to the hydrochloride, m.p. 137° C.

Workup

  1. temperatureThe mixture is heated for 6 hours
  2. customAfter purification by flashchromatography on a silica column

Sources & evidence

ORD record
ord-7f91fe0b8ee84803af6a230efec11ab9
Source dataset
uspto-grants-1991_06
Patent number
US05021420

Reaction notes

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