HCID 12851454, compound → HCID 12851455, compound

HRID 1156591Notes

Reaction equation

HRID 1156591 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:30])[CH2:9][CH2:10][C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][C:14]=1[C:22]1[C:23]([CH2:28][CH3:29])=[N:24][O:25][C:26]=1[CH3:27])=[O:12]>O1CCCC1>[CH3:30][N:8]([CH3:7])[CH2:9][CH2:10][CH:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][C:14]=1[C:22]1[C:23]([CH2:28][CH3:29])=[N:24][O:25][C:26]=1[CH3:27])[OH:12]

Participants

4

Reactant 2

HCID 12851454HCID 12851454, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12851455HCID 12851455, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 816 mg. (0.022 mole) of lithium aluminum hydride in 125 ml. tetrahydrofuran is cooled to 5° and treated by the dropwise addition of 3.5 g. (0.011 mole) of 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanone in 125 ml. tetrahydrofuran maintaining the temperature between 5°-8° C. The resulting mixture is then stirred for 4 hours at 0°-5°, then cooled to -50° and quenched by the addition of 10 ml. saturated magnesium sulfate solution. The mixture is warmed to room temperature and filtered and the filtrate is evaporated in vacuo. The resulting residue is dissolved in methylene chloride, washed with water, dried over magnesium sulfate, filtered and evaporated in vacuo. The residue is crystallized from ether to give 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanol, m.p. 166°-169° C.

Workup

  1. additionA suspension of 816 mg
  2. additiontreated by the dropwise addition of 3.5 g
  3. custombetween 5°-8° C
  4. temperaturecooled to -50°
  5. customquenched by the addition of 10 ml
  6. filtrationfiltered
  7. customthe filtrate is evaporated in vacuo
  8. dissolutionThe resulting residue is dissolved in methylene chloride
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated in vacuo
  13. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-e7e2b6cb3c404842a63efb0618b7aa83
Source dataset
uspto-grants-1982_06
Patent number
US04336391

Reaction notes

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