Sodium Iodide → HCID 10768312, compound

HRID 1594799Notes

Reaction equation

HRID 1594799 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[S:8][CH2:7]1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]([N:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[CH:25]2)=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC#N>[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]([N:33]3[CH2:34][CH2:35][N:36]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]4[C:10](=[O:11])[C:9]5([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]5)[S:8][CH2:7]4)[CH2:37][CH2:38]3)=[CH:25]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 10542663HCID 10542663, compoundHCID 10589970HCID 10589970, compound

Product 1

HCID 10768312HCID 10768312, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(4-bromobutyl)-1-thia-3-azaspiro[4.5]decan-4-one (3.8 g), 1-(4-fluorophenyl)-3-piperazino-1H-indole (3.7 g), K2CO3 (3.5 g), NaI (200 mg) and anhydrous CH3CN (150 ml) was heated to 80° C. with stirring under nitrogen. After 18 hours, no starting amine remained as judged by TLC. The mixture was cooled to room temperature and filtered, and the filtrate concentrated in vacuo. The residue was chromatographed on silica using EtOAc as an eluent. The fractions containing the desired product were combined and concentrated to provide a foam which was recrystallized from ether to provide 2.816 g of crystals, m.p. 134-136° C., homogeneous by TLC.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was chromatographed on silica
  5. additionThe fractions containing the desired product
  6. concentrationconcentrated
  7. customto provide a foam which
  8. customwas recrystallized from ether

Sources & evidence

ORD record
ord-887b06c76011415fb53b09280afec239
Source dataset
uspto-grants-2001_09
Patent number
US06284775B1

Reaction notes

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