Triethylamine → Fananserin

HRID 1087476Notes

Reaction equation

HRID 1087476 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].C(N(CC)CC)C.[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1>C1(C)C=CC=CC=1>[F:26][C:27]1[CH:28]=[CH:29][C:30]([N:33]2[CH2:38][CH2:37][N:36]([CH2:2][CH2:3][CH2:4][N:5]3[C:9]4[CH:10]=[CH:11][CH:12]=[C:13]5[CH:14]=[CH:15][CH:16]=[C:7]([C:8]=45)[S:6]3(=[O:18])=[O:17])[CH2:35][CH2:34]2)=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752601-(4-Fluorophenyl)piperazineHCID 145800262(3-Chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide

Product 1

HCID 60785Fananserin

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(3-Chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (28.1 g), triethylamine (14 cc) and 1-(4-fluorophenyl)piperazine (18.8 g) in toluene (300 cc) are heated for 8 hours at boiling point. The mixture is then cooled to a temperature of about 20.C and stirring is maintained for 15 hours at this temperature. The precipitate formed is separated by filtration and washed with toluene (2×50 cc). The filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue obtained is purified by flash-chromatography on a silica column, under a current of argon at medium pressure (0.1-1.5 bar) with ethyl acetate as eluant, and recrystallized from boiling acetonitrile (150 cc). 2-{3-[4-(4-Fluorophenyl)-1-piperazinyl]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide is obtained, m.p. 95°-97° C.

Workup

  1. temperatureis maintained for 15 hours at this temperature
  2. customThe precipitate formed
  3. customis separated by filtration
  4. washwashed with toluene (2×50 cc)
  5. customThe filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  6. customThe residue obtained
  7. customis purified by flash-chromatography on a silica column
  8. customunder a current of argon at medium pressure (0.1-1.5 bar) with ethyl acetate as eluant, and recrystallized

Sources & evidence

ORD record
ord-bf627f542a43417197b1393dd50ce878
Source dataset
uspto-grants-1991_07
Patent number
US05036075

Reaction notes

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