Tetrahydrofuran → N,N-Dimethyl-2-(5-methyl-3-phenyl-4-isoxazolyl)-1H-indole-3-ethanamine

HRID 1649083Notes

Reaction equation

HRID 1649083 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH3:12][N:13]([CH3:39])[C:14](=O)[C:15]([C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][C:18]=1[C:26]1[C:27]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[N:28][O:29][C:30]=1[CH3:31])=O>O>[CH3:31][C:30]1[O:29][N:28]=[C:27]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]=1[C:18]1[NH:19][C:20]2[C:25]([C:17]=1[CH2:15][CH2:14][N:13]([CH3:39])[CH3:12])=[CH:24][CH:23]=[CH:22][CH:21]=2

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 12854865HCID 12854865, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12854866N,N-Dimethyl-2-(5-methyl-3-phenyl-4-isoxazolyl)-1H-indole-3-ethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a refluxing suspension of 22.8 g. (0.60 mole) of lithium aluminum hydride in 1100 ml. of tetrahydrofuran under nitrogen, there is added dropwise over approximately 1 to 11/2 hours a warm solution of 56 g. (0.15 mole) of N,N-dimethyl-2-(5-methyl-3-phenyl-4-isoxazolyl)-3-indoleglyoxylamide in 2250 ml. of tetrahydrofuran. The mixture is refluxed for 3 hours after addition is completed. The resulting suspension is cooled to -10° to +5° C. and a solution of 270 ml. of tetrahydrofuran and 90 ml. of water is added dropwise with the temperature maintained between -10° and +5° C. The suspension is stirred for approximately 1 hour without a cooling bath and then allowed to stand overnight without stirring. The mixture is filtered, the filtrate evaporated in vacuo and the residue dissolved in methylene chloride. The methylene chloride is washed with water, dried and evaporated in vacuo. The residue is crystallized from ether to give 2-(5-methyl-3-phenyl-4-isoxazolyl)-3-(dimethylaminoethyl)-indole; m.p. 141.5° to 143.5° C.

Workup

  1. additionTo a refluxing suspension of 22.8 g
  2. temperatureThe mixture is refluxed for 3 hours
  3. additionafter addition
  4. temperatureThe resulting suspension is cooled to -10° to +5° C.
  5. temperaturemaintained between -10° and +5° C
  6. waitto stand overnight
  7. stirringwithout stirring
  8. filtrationThe mixture is filtered
  9. customthe filtrate evaporated in vacuo
  10. dissolutionthe residue dissolved in methylene chloride
  11. washThe methylene chloride is washed with water
  12. customdried
  13. customevaporated in vacuo
  14. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-0c06efdbb77242ddbf7b4cb715c8eb1f
Source dataset
uspto-grants-1983_11
Patent number
US04415568

Reaction notes

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