Sodium Bicarbonate → HCID 15646696, compound

HRID 1196609Notes

Reaction equation

HRID 1196609 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[CH:5]2.Cl[CH2:19][CH2:20][N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[CH:30]=[CH:31][CH:32]=[C:23]([C:24]=23)[S:22]1(=[O:34])=[O:33].C(=O)([O-])O.[Na+]>O1CCCC1.CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:19][CH2:20][N:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[C:29]5[CH:30]=[CH:31][CH:32]=[C:23]([C:24]=45)[S:22]3(=[O:34])=[O:33])[CH2:16][CH2:17]1)=[CH:5]2

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 98345611H-Indole, 5-fluoro-2-(4-piperidinylmethyl)-HCID 145800412-(2-Chloroethyl)naphtho[1,8-cd]isothiazole 1,1-dioxide

Product 1

HCID 15646696HCID 15646696, compoundYield 39.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[(5-fluoro-2-indolyl)methyl]piperidine (2.9 g), 2-(2-chloroethyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (3.5 g) and sodium hydrogen carbonate (1.1 g) in tetrahydrofuran (30 cc) and dimethylformamide (30 cc) is brought to reflux for 12 hours. After evaporation to dryness at 80° C. under reduced pressure (20 mm Hg; 2.7 kPa), the residue is taken up with water (150 cc) and extracted with ethyl acetate (2×75 cc). The combined organic phases are dried over magnesium sulphate and taken to dryness at 80° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is purified by flash chromatography on a silica column under a stream of nitrogen at moderate pressure (0.5-1.5 bar) with a cyclohexane/ethyl acetate mixture (50:50 by volume) as eluent. 2-{2-[4-((5-Fluoro-2-indolyl)methyl)piperidino]ethyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (2.3 g), m.p. 154° C., is obtained.

Workup

  1. temperatureto reflux for 12 hours
  2. customAfter evaporation to dryness at 80° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  3. extractionextracted with ethyl acetate (2×75 cc)
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. customtaken to dryness at 80° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  6. customThe residue is purified by flash chromatography on a silica column under a stream of nitrogen at moderate pressure (0.5-1.5 bar) with a cyclohexane/ethyl acetate mixture (50:50 by volume) as eluent

Sources & evidence

ORD record
ord-383043cf388f425d9bf4da3c2b30051f
Source dataset
uspto-grants-1992_05
Patent number
US05114949

Reaction notes

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