Water → 3-amino-N,N-dimethylbenzylamine

HRID 1740799Notes

Reaction equation

HRID 1740799 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:18])[C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1.O.[OH-].[Na+]>O1CCCC1>[CH3:18][N:8]([CH2:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[NH2:16])[CH3:7]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 4247743-Amino-N,N-dimethylbenzamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 992943-amino-N,N-dimethylbenzylamineYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred suspension of lithium aluminium hydride (0.24 g, 6.3 mmol) in tetrahydrofuran (THF) (15 ml) at 0° C. under Argon, was treated dropwise over a period of fifteen minutes, with a solution of N,N-Dimethyl-3-aminobenzamide (D24) (0.68 g, 4.2 mmol) in THF (15 ml). The reaction mixture was allowed to warm to room temperature after which it was heated to reflux for 2 hours. The reaction mixture was allowed to cool to room temperature then treated sequentially with water (0.24 ml), 10% sodium hydroxide solution (0.24 ml) then water (0.72 ml). The reaction mixture was filtered through kieselguhr and the filtrate dried (Na2SO4) and concentrated in vacuo to afford the title compound as a pale brown oil (0.55 g, 87%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. temperatureto cool to room temperature
  4. filtrationThe reaction mixture was filtered through kieselguhr
  5. dry with materialthe filtrate dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47f563aeb5b44632938ba14dbe2338da
Source dataset
uspto-grants-1999_10
Patent number
US05972937

Reaction notes

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