Potassium Bromide → HCID 178479774, compound

HRID 1154719Notes

Reaction equation

HRID 1154719 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:19][C:20]1[C:24]2[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:23]=2[S:22](=[O:31])(=[O:30])[N:21]=1.[K+].[Br-]>C(Cl)(Cl)Cl>[ClH:19].[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]=[C:26]([F:29])[CH:27]=[CH:28][C:23]=3[S:22](=[O:30])(=[O:31])[N:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 13390872HCID 13390872, compound

Product 1

HCID 178479774HCID 178479774, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a refluxing solution of 3-[3-(1-piperidinylmethyl)phenoxy]propylamine (0.870 g, 3.503 mmoles) in dried chloroform (35 ml) under dry nitrogen is added over 45 minutes a solution of 3-chloro-5-fluoro-1,2-benzisothiazole 1,1-dioxide (0.808 g, 3.679 mmoles) in dried chloroform (20 ml) while maintaining reflux. After the addition is complete refluxing is continued for 15 minutes and the solution allowed to come to room temperature. Evaporation in vacuo gives an orange solid. Recrystallization from isopropanol gives a light tan solid. m.p. 224°-226° after softening from 200° C. IR (KBr) 2950, 1600, 1302, 1171 cm-1 ; NMR (in DMSO) 1.76 (6H,s), 2.2 (2H,t), 2.8 (2H,m), 3.3 (3H,m), 3.6 (2H,t), 4.2 (3Hm,), 7.0-8.5 (7H,m), 10.1 (1h,s), 10.6 (1H,m).

Workup

  1. temperaturewhile maintaining
  2. temperaturereflux
  3. additionAfter the addition
  4. temperatureis complete refluxing
  5. customto come to room temperature
  6. customEvaporation in vacuo
  7. customgives an orange solid
  8. customRecrystallization from isopropanol
  9. customgives a light tan solid
  10. customafter softening from 200° C

Sources & evidence

ORD record
ord-0a52d6250ca14a208065097e44985a12
Source dataset
uspto-grants-1984_12
Patent number
US04490527

Reaction notes

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