Sodium Iodide → 8-Azaspiro(4.5)decane-7,9-dione, 8-(4-(4-(5-methoxy-1H-indol-3-yl)-1-piperidinyl)butyl)-
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.ClCCCC[CH:23]1[C:27]2([CH2:32][C:31](=[O:33])[NH:30][C:29](=[O:34])[CH2:28]2)[CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].[CH3:43][C:44](=O)[CH2:45][CH3:46]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:12]1[CH2:17][CH2:16][N:15]([CH2:43][CH2:44][CH2:45][CH2:46][N:30]2[C:29](=[O:34])[CH2:28][C:27]3([CH2:23][CH2:24][CH2:25][CH2:26]3)[CH2:32][C:31]2=[O:33])[CH2:14][CH2:13]1Participants
6
Procedure
A mixture of 2.3 g of 5-methoxy-3-(4-piperidinyl)-1H-indole, 2.58 g of 8-[4-chlorobutyl-8-azaspiro[4,5]decane-7,9-dione, 2.12 g of sodium carbonate, 150 mg of sodium iodide and 50 ml of butanone was refluxed under an inert atmosphere with stirring for 20 hours and after another 1.29 g of the dione were added. Reflux was continued for 6 hours. The mixture was filtered and washed with acetone and the filtrate was evaporated to dryness. The residue was crystallized from 60% ethanol to obtain 3.4 g of 8-[4-{4-(5-methoxy-1H-indol-3-yl)-1-piperidinyl}-butyl]-8-azaspiro[4,5]decane-7,9-dione melting at ≈150° C.
Workup
- temperaturewas refluxed under an inert atmosphere
- additionafter another 1.29 g of the dione were added
- temperatureReflux
- waitwas continued for 6 hours
- filtrationThe mixture was filtered
- washwashed with acetone
- customthe filtrate was evaporated to dryness
- customThe residue was crystallized from 60% ethanol
Sources & evidence
- ORD record
- ord-fd829c56d3214d779d39c0b9dbfe9085
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04855302
Reaction notes
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