1,4-Dibromobutane → HCID 13232499, compound

HRID 648196Notes

Reaction equation

HRID 648196 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

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-benzoisothiazol-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-23ea34af85ad483184a687aab2b757bf
Source dataset
uspto-grants-1983_10
Patent number
US04411901

Reaction notes

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