HCID 12851454, compound → HCID 13520520, compound

HRID 1380576Notes

Reaction equation

HRID 1380576 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:16]1[C:17]([CH2:22][CH3:23])=[N:18][O:19][C:20]=1[CH3:21])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:22]([C:17]1[C:16]([C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:24])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:20]([CH3:21])[O:19][N:18]=1)[CH3:23]

Participants

4

Reactant 2

HCID 12851454HCID 12851454, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13520520HCID 13520520, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 5.0 grams (0.015 mole) of 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanone in 120 milliliters of tetrahydrofuran is added dropwise to a refluxing mixture of 2.0 grams of lithium aluminum hydride (0.053 mole) and 200 ml. of tetrahydrofuran under nitrogen. The combined mixture is refluxed for one hour, cooled in an ice bath and quenched by the cautious addition of 7 milliliters of water. The mixture is then filtered through celite and the solvent evaporated in vacuo to yield an oil, which slowly crystallizes. The crystals are triturated with ether to give 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-(3-dimethylaminopropyl)-indole, m.p. 131°-133° C.

Workup

  1. temperatureThe combined mixture is refluxed for one hour
  2. temperaturecooled in an ice bath
  3. customquenched by the cautious addition of 7 milliliters of water
  4. filtrationThe mixture is then filtered through celite
  5. customthe solvent evaporated in vacuo
  6. customto yield an oil, which
  7. customslowly crystallizes
  8. customThe crystals are triturated with ether

Sources & evidence

ORD record
ord-6b911f9300d5495580c12d1e9ca885f2
Source dataset
uspto-grants-1986_04
Patent number
US04582848

Reaction notes

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