HCID 13187620, compound → HCID 13187621, compound

HRID 434501Notes

Reaction equation

HRID 434501 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:31])[C:9](=O)[C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH3:21])[C:13]=1[C:22]1[C:23]([CH2:28][CH3:29])=[N:24][O:25][C:26]=1[CH3:27])=[O:11]>O1CCCC1.C(OCC)C>[CH3:31][N:8]([CH2:9][CH:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH3:21])[C:13]=1[C:22]1[C:23]([CH2:28][CH3:29])=[N:24][O:25][C:26]=1[CH3:27])[OH:11])[CH3:7]

Participants

5

Reactant 2

HCID 13187620HCID 13187620, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13187621HCID 13187621, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 9.24 g (0.243 mole) of lithium aluminum hydride and 500 ml tetrahydrofuran under nitrogen is heated to reflux and is treated by rapid addition with 18.47 g (0.054 mole) of N,N,1-trimethyl-2-(3-ethyl-5-methyl-4-isoxazolyl)-3-indoleglyoxylamide in 350 ml of tetrahydrofuran. The resulting mixture is heated an additional 15 minutes, cooled, diluted with 350 ml of diethylether and is quenched by the dropwise addition of 60 ml of saturated magnesium sulfate solution. The mixture is then filtered through celite and the filter cake is washed with tetrahydrofuran methylene chloride and methanol. The filtrate is evaporated in vacuo and the residue chromatographed on silica gel using acetone as an eluant to give α-(dimethylaminomethyl)-2-(3-ethyl-5-methyl-4-isoxazolyl)-1-methyl-indole-3-methanol m.p. 119° to 121° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. temperatureThe resulting mixture is heated an additional 15 minutes
  4. temperaturecooled
  5. customis quenched by the dropwise addition of 60 ml of saturated magnesium sulfate solution
  6. filtrationThe mixture is then filtered through celite
  7. washthe filter cake is washed with tetrahydrofuran methylene chloride and methanol
  8. customThe filtrate is evaporated in vacuo
  9. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-fdc2fb0a87aa4ea9ad059575c1e550dd
Source dataset
uspto-grants-1983_08
Patent number
US04397850

Reaction notes

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