Potassium Iodide → HCID 12614468, compound

HRID 2166108Notes

Reaction equation

HRID 2166108 reaction equation
Br[CH2:2][CH2:3][S:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[CH2:6]1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.[C:26](=[O:29])([OH:28])[O-].[Na+].[I-].[K+]>CN(C)C=O.O>[C:10]([OH:9])(=[O:23])[C:26]([OH:28])=[O:29].[O:23]1[CH2:24][CH2:25][N:20]([CH2:2][CH2:3][S:4][CH:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][C:8]3[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=3[CH2:6]2)[CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 12614445HCID 12614445, compound

Product 1

HCID 12614468HCID 12614468, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g of 10-(β-bromoethylthio)-10,11-dihydrodibenz[b,f]oxepin, Example 3, 0.5 g of morpholine, 1.0 g of sodium bicarbonate and 1.0 g of potassium iodide in 15 ml of dimethylformamide is stirred at 60°-70° C. for 64 hours. The reaction mixture is permitted to cool before being diluted with water. The biphasic mixture is extracted with ether and the combined ether extracts are shaken with a large excess of 2N hydrochloric acid. The acid solution is basified with potassium carbonate liberating the amine as an oil which is extracted into ether. The ethereal solution is dried and the ether is removed under vacuum regenerating an oil which is converted to its oxalate. The salt is recrystallized from a methanol-acetone-ether mixture to give colorless plates, mp 196°-198° C. of 10,11-dihydro-10-(β-morpholinoethylthio)dibenz[b,f]oxepin oxalate.

Workup

  1. temperatureto cool
  2. extractionThe biphasic mixture is extracted with ether
  3. stirringthe combined ether extracts are shaken with a large excess of 2N hydrochloric acid
  4. extractionis extracted into ether
  5. customThe ethereal solution is dried
  6. customthe ether is removed under vacuum
  7. customThe salt is recrystallized from a methanol-acetone-ether mixture

Sources & evidence

ORD record
ord-154e6c865e2c4d2db1c2d6ed91dac356
Source dataset
uspto-grants-1990_07
Patent number
US04943571

Reaction notes

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