Sodium Hydroxide → HCID 64502553, compound

HRID 220255Notes

Reaction equation

HRID 220255 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:13][CH2:14][C:15]([NH:17][CH3:18])=O)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:13][CH2:14][CH2:15][NH:17][CH3:18])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68413945HCID 68413945, compound

Product 1

HCID 64502553HCID 64502553, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 0.26 g of 3-(3,4-diethoxy-phenyl)-N-methyl-propionamide in 5 mL THF was added 1.4 mL of a LiAlH4 solution (2.3M in THF) at 0° C. The reaction mixture was stirred for 1 h at rt and for 2 h at 60° C. At rt, a 1M NaOH solution was added dropwise. The resulting mixture was filtrated over a pad of celite, washed with THF and the filtrate concentrated in vacuo. Purification by CC with EtOAc-MeOH (7:3) yielded 0.13 g of [3-(3,4-diethoxy-phenyl)-propyl]-methyl-amine as yellow oil.

Workup

  1. filtrationThe resulting mixture was filtrated over a pad of celite
  2. washwashed with THF
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification by CC with EtOAc-MeOH (7:3)

Sources & evidence

ORD record
ord-a5429fff38994cbd8c295796424a9ac9
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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