1H-Indole, 3-(4-piperidinylmethyl)- (9CI) → HCID 19898897, compound

HRID 1196610Notes

Reaction equation

HRID 1196610 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:2]1.Cl[CH2:18][CH2:19][N:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[C:28]3[CH:29]=[CH:30][CH:31]=[C:22]([C:23]=23)[S:21]1(=[O:33])=[O:32].C(=O)([O-])O.[Na+]>CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:18][CH2:19][N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[C:28]5[CH:29]=[CH:30][CH:31]=[C:22]([C:23]=45)[S:21]3(=[O:33])=[O:32])[CH2:13][CH2:12]2)=[CH:2]1

Participants

5

Reactant 3

HCID 190261H-Indole, 3-(4-piperidinylmethyl)- (9CI)HCID 516892Sodium BicarbonateHCID 145800412-(2-Chloroethyl)naphtho[1,8-cd]isothiazole 1,1-dioxide

Product 1

HCID 19898897HCID 19898897, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-indolylmethyl)piperidine (0.4 g), 2-(2-chloroethyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (0.53 g), sodium hydrogen carbonate (0.17 g) and dimethylformamide (10 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 (30 cc) and extracted with ethyl acetate (2×50 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 dichloromethane/methanol mixture (99:1 by volume) as eluent. 2-{2-[4-(3-Indolylmethyl)piperidino]ethyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (0.4 g), m.p. 184° 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 (2×50 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 dichloromethane/methanol mixture (99:1 by volume) as eluent

Sources & evidence

ORD record
ord-74aae76942d04ce9a973884fce185358
Source dataset
uspto-grants-1992_05
Patent number
US05114949

Reaction notes

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