Hydrochloric Acid → HCID 14535921, compound

HRID 1090073Notes

Reaction equation

HRID 1090073 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([C:9]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)=[O:10])=[CH:7][CH:6]=1.[Cl:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.Cl>CCCCCC.CN(C=O)C.COC(C)(C)C.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.O>[ClH:22].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][N:15]3[CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:10])=[CH:20][CH:21]=1

Participants

11

Reactant 4

HCID 313Hydrochloric Acid2×HCID 24758Sodium hydrideHCID 767274-(2-Chloroethyl)morpholineHCID 14535919HCID 14535919, compound

Product 1

HCID 14535921HCID 14535921, compoundYield 70.2%

Reagents, catalysts & solvents 6

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 15413tert-Butyl methyl etherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred mixture of 3.5 g (0.0887 mole) of a 60% suspension of sodium hydride in hexane in 50 ml of DMF was added 18.1 g (0.0721 mole) of 4-(4-methoxybenzoyl)indole. The mixture was treated with a solution containing 0.18 mole of 4-(2-chloroethyl)morpholine in t-butyl methyl ether (prepared by extraction of the free base from a suspension of 35.5 g of the corresponding hydrochloride in saturated sodium bicarbonate). When addition was complete, the reaction mixture was heated under reflux for about twelve hours, treated with 1500 ml of water and extracted with 500 ml of ethyl acetate. The combined organic extracts, on drying and evaporation to dryness, afforded an oil which was dissolved in 250 ml of ethyl acetate and treated with 50 ml of ethereal hydrogen chloride. The material which separated was collected and recrystallized from ethanol to give 20.3 g of 4-(4-methoxybenzoyl)-1-[2-(4-morpholinyl)ethyl]-1H-indole hydrochloride, m.p. 177°-180° C.

Workup

  1. additionThe mixture was treated with a solution
  2. additionWhen addition
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for about twelve hours
  5. extractionextracted with 500 ml of ethyl acetate
  6. customThe combined organic extracts, on drying
  7. customevaporation to dryness
  8. customafforded an oil which
  9. customThe material which separated
  10. customwas collected
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d5945fa50fc3406c9ef248c0f54288fb
Source dataset
uspto-grants-1992_01
Patent number
US05081122

Reaction notes

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