Aluminium lithium hydride → N-methyl-N-(8-phenyloctyl)amine

HRID 1884765Notes

Reaction equation

HRID 1884765 reaction equation
[CH3:1][NH:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22237455N-methyl-8-phenyloctanamide

Product 1

HCID 22237633N-methyl-N-(8-phenyloctyl)amineYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methyl-8-phenyloctanamide (25.2 g, 108.0 mmol, 1 eq) in THF (500 mL) cooled to 0° C. was added lithium aluminum hydride (12.3 g, 466.8 mmol, 4.3 eq) portionwise over 20 minutes. The cold bath was removed and the reaction was stirred at rt 3 hours. The reaction was then heated at reflux for 2 _hours. It was then cooled to rt and quenched by the slow addition of H2O (30 mL). EtOAc (300 mL) was added, followed by 2 M NaOH (40 mL). The solids were then filtered off and washed with EtOAc. The filtrate was dried over MgSO4 and concentrated in vacuo to afford N-methyl-N-(8-phenyloctyl)amine (19.7 g, 83%) as a light yellow oil. 1H NMR (CDCl3) δ 7.30-7.14 (m, 5H); 2.63-2.52 (m, 4H); 2.43 (s, 3H); 2.05 (s, 1H); 1.62 (m, 4H); 1.30 (m, 8H).

Workup

  1. customThe cold bath was removed
  2. temperatureThe reaction was then heated
  3. temperatureat reflux for 2 _hours
  4. temperatureIt was then cooled to rt
  5. customquenched by the slow addition of H2O (30 mL)
  6. additionEtOAc (300 mL) was added
  7. filtrationThe solids were then filtered off
  8. washwashed with EtOAc
  9. dry with materialThe filtrate was dried over MgSO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8069d09a10a84bb8aeb573586011b0f1
Source dataset
uspto-grants-2004_07
Patent number
US06765021B2

Reaction notes

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