HCID 13520517, compound → HCID 13520518, compound

HRID 485320Notes

Reaction equation

HRID 485320 reaction equation
[CH3:1][N:2]([CH3:28])[C:3](=O)[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[C:15]1[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:17][O:18][C:19]=1[CH3:20].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:20][C:19]1[O:18][N:17]=[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]=1[C:7]1[NH:8][C:9]2[C:14]([C:6]=1[CH2:5][CH2:4][CH2:3][N:2]([CH3:28])[CH3:1])=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 2

HCID 13520517HCID 13520517, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13520518HCID 13520518, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.0 g (0.0054 mole) of N,N-dimethyl-2-(5-methyl-3-phenyl-4-isoxazolyl)-3-indole propionamide in 80 ml tetrahydrofuran is added to a suspension of 0.82 g (0.0216 mole) of lithium aluminum hydride in 40 ml tetrahydrofuran dropwise, maintaining the temperature between 20° and 25° C. After the addition is complete the mixture is stirred at room temperature for two hours, cooled and quenched by the addition of 2 ml of water in 20 ml tetrahydrofuran. The resulting mixture is dried over magnesium sulfate, filtered and evaporated. The solid residue is recrystallized from ethanol to give 2-(5-methyl-3-phenyl-4-isoxazolyl)-3-(3-dimethylaminopropyl)-indole m.p. 156° to 157° C.

Workup

  1. temperaturemaintaining the temperature between 20° and 25° C
  2. additionAfter the addition
  3. temperaturecooled
  4. customquenched by the addition of 2 ml of water in 20 ml tetrahydrofuran
  5. dry with materialThe resulting mixture is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-83a0a450de614dc798a1958b01f60158
Source dataset
uspto-grants-1985_08
Patent number
US04536499

Reaction notes

Loading…