1,4-Dibromobutane → HCID 13232499, compound

HRID 1262544Notes

Reaction equation

HRID 1262544 reaction equation
[N:1]1([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Br:16][CH2:17][CH2:18][CH2:19][CH2:20]Br.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Br-:16].[S:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:7]([N:1]2[CH2:6][CH2:5][N+:4]3([CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:3][CH2:2]2)=[N:8]1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazole

Product 1

HCID 13232499HCID 13232499, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Method B--A mixture of 3-(1-piperazinyl)-1,2-benzisothiazole (5.0 g., 0.0228 mole), 1,4-dibromobutane (9.8 g., 0.0456 mole) and finely powdered anhydrous potassium carbonate (7.9 g., 0.057 mole) in 100 ml. of ethanol is stirred and refluxed for a 16 hr. period. The cooled reaction mixture is filtered and the filtrate concentrated in vacuo. Residual solid heated to reflux with 70 ml. of isopropanol and filtered. Concentration of the filtrate to about one-half volume and refrigeration affords 5.58 g. (69.1% yield) of 8-(1,2-benzisothiazol-3-yl)-8-aza-5-azoniaspiro[4.5]decane bromide, m.p. 246.5°-253° C.

Workup

  1. temperaturerefluxed for a 16 hr
  2. customThe cooled reaction mixture
  3. filtrationis filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. temperatureResidual solid heated
  6. temperatureto reflux with 70 ml
  7. filtrationof isopropanol and filtered
  8. customConcentration of the filtrate to about one-half volume and refrigeration affords 5.58 g

Sources & evidence

ORD record
ord-b62709017fc04b1383c5c80df1f75673
Source dataset
uspto-grants-1984_06
Patent number
US04452799

Reaction notes

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