HCID 18469818, compound → HCID 11392790, compound

HRID 2228416Notes

Reaction equation

HRID 2228416 reaction equation
[CH3:1][NH:2][C:3](=O)[CH2:4][CH:5]([CH2:7][CH2:8][CH2:9][CH:10]([CH2:12][CH2:13][CH2:14][CH:15]([CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:16])[CH3:11])[CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([CH2:7][CH2:8][CH2:9][CH:10]([CH2:12][CH2:13][CH2:14][CH:15]([CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:16])[CH3:11])[CH3:6]

Participants

4

Reactant 2

HCID 18469818HCID 18469818, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11392790HCID 11392790, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-methylphytanamide (4.0 g) and lithium aluminium hydride (pellets 95%, 2.0 g) in tetrahydrofuran (100 ml) was heated under reflux for two hours. The reaction mixture cooled, excess lithium aluminium hydride destroyed, and solid salts were filtered off. The crude product was dissolved in dichloromethane and washed with water, dried (MgSO4) and the solvent removed. The crude product was chromatographed on flash silica (1% aqueous ammonia, 10-20% methanol in dichloromethane ) to give pure N-methylphytanamine as a colourless liquid. Yield 2.08 g, 54%. 1H-n.m.r. (CDCl3) δ0.82-1.5(m, 39H, phyt), 2.439 (s, 3H, NCH3), 2.54 (m, 2H, CH2CH2NH).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for two hours
  3. temperatureThe reaction mixture cooled
  4. customexcess lithium aluminium hydride destroyed
  5. filtrationsolid salts were filtered off
  6. dissolutionThe crude product was dissolved in dichloromethane
  7. washwashed with water
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed
  10. customThe crude product was chromatographed on flash silica (1% aqueous ammonia, 10-20% methanol in dichloromethane )

Sources & evidence

ORD record
ord-468f800a89eb47039e8b4113e6b63422
Source dataset
uspto-grants-2002_07
Patent number
US06417009B1

Reaction notes

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