Water → HCID 20203539, compound

HRID 1732065Notes

Reaction equation

HRID 1732065 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[CH2:11][CH2:12][CH2:13][CH:14]([N:15]([CH:18]([CH3:20])[CH3:19])[CH:16]=O)[C:3]=12.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH:14]1[C:3]2=[C:2]([CH3:1])[C:10]3[C:5]([N:4]2[CH2:11][CH2:12][CH2:13]1)=[CH:6][CH:7]=[CH:8][CH:9]=3

Participants

5

Reactant 3

HCID 962WaterHCID 20203550HCID 20203550, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20203539HCID 20203539, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(6,7,8,9-tetrahydro-10-methylpyrido[1,2-a]indol-9-yl)-N-(1-methylethyl)formamide (37.1 mmol) in tetrahydrofuran (50 mL) was added dropwise at 25° C. to a suspension of lithium aluminum hydride (1.6 g, 42.1 mmol) in the same solvent (50 mL). The reaction mixture was refluxed overnight under the exclusion of moisture. The metal complex was decomposed with a solution of water (3 mL) in the (20 mL) under nitrogen. The resulting suspension was filtered and the filtrate evaporated in vacuo. The residue was dissolved in CHCl3 (100 mL), dried over MgSO4, filtered, and evaporated in vacuo. The oily residue was chromatographed on silica gel (200 g). Elution with 2% MeOH in CHCl3 afforded the title base.

Workup

  1. temperatureThe reaction mixture was refluxed overnight under the exclusion of moisture
  2. filtrationThe resulting suspension was filtered
  3. customthe filtrate evaporated in vacuo
  4. dissolutionThe residue was dissolved in CHCl3 (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe oily residue was chromatographed on silica gel (200 g)
  9. washElution with 2% MeOH in CHCl3

Sources & evidence

ORD record
ord-4e6bfb6b02d94a14a73ffcf095eff69c
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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