Pseudosaccharin chloride → HCID 178527194, compound

HRID 1154716Notes

Reaction equation

HRID 1154716 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[S:22](=[O:30])(=[O:29])[N:21]=1>C(Cl)(Cl)Cl>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[S:22](=[O:29])(=[O:30])[N:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 64783Pseudosaccharin chlorideHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 178527194HCID 178527194, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a gently refluxing solution of 3-[3-[(1-piperidinyl)-methyl]phenoxy]propylamine (992 mg, 4 mmol) in 90 ml of chloroform is added dropwise a solution of 880 mg (4.4 mmol) of 3-chlorobenzisothiazole 1, 1-dioxide in 30 ml of chloroform. Following the addition, the reaction mixture is refluxed for an additional 15 min., cooled to room temperature and solvent removed in vacuo. Column chromatography of the resultant residue (foam) on silica gel utilizing methylene chloride:methanol:ammonium hydroxide (90:10:1) as eluting solvent affords after evaporation a white solid. The crude product is suspended in ethyl acetate, filtered and dried to give 620 mg (37.5%) of the title compound, m.p., 138°-140° C.

Workup

  1. additionthe addition
  2. temperaturethe reaction mixture is refluxed for an additional 15 min.
  3. customsolvent removed in vacuo
  4. washColumn chromatography of the resultant residue (foam) on silica gel utilizing methylene chloride:methanol:ammonium hydroxide (90:10:1) as eluting solvent
  5. customaffords
  6. customafter evaporation a white solid
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-90f3428317ca43ff824a8a98d60d6a3f
Source dataset
uspto-grants-1984_12
Patent number
US04490527

Reaction notes

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