Potassium Iodide → Tiospirone

HRID 1262543Notes

Reaction equation

HRID 1262543 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[CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[C:30](=[O:31])[CH2:29][C:24]2([CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:23][C:22]1=[O:32].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[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]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]3[C:22](=[O:32])[CH2:23][C:24]4([CH2:28][CH2:27][CH2:26][CH2:25]4)[CH2:29][C:30]3=[O:31])[CH2:3][CH2:2]2)=[N:8]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 112088518-(4-Bromobutyl)-8-azaspiro(4.5)decane-7,9-dione

Product 1

HCID 55752Tiospirone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Method A--A mixture of 3-(1-piperazinyl)-1,2-benzisothiazole (24.3 g., 0.11 mole) and 8-(4-bromobutyl)-8-azaspiro[4.5]decane-7.9-dione (33.5 g., 0.11 mole), anhydrous potassium carbonate (32.4 g., 0.23 mole) and potassium iodide (3.9 g., 0.023 mole) in 1 liter of acetonitrile is stirred and heated under reflux for a period of 20 hr. The reaction mixture is filtered, concentrated in vacuo and residual material taken up in 350 ml. of chloroform which is filtered and concentrated in vacuo. The residue is triturated with ether, refrigerated and resulting solid collected. This material crystallized from acetonitrile (employing activated charcoal affords a first crop 25.1 g, m.p. 120°-124° C. and a second crop, 6.0 g, m.p. 123°-126° C. for a total yield of 31.1 g. (64% yield) of the free base form of the title compound. Crystallization from acetonitrile affords analytically pure 8-[4-[ 4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione, m.p. 124°-126° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for a period of 20 hr
  3. filtrationThe reaction mixture is filtered
  4. concentrationconcentrated in vacuo and residual material
  5. filtrationof chloroform which is filtered
  6. concentrationconcentrated in vacuo
  7. customThe residue is triturated with ether
  8. customrefrigerated and resulting solid
  9. customcollected
  10. customThis material crystallized from acetonitrile (
  11. customaffords a first crop 25.1 g, m.p. 120°-124° C.

Sources & evidence

ORD record
ord-6af7773a67a0461ba856346420b43ef1
Source dataset
uspto-grants-1984_06
Patent number
US04452799

Reaction notes

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