Sodium Hydroxide → 3,4-Dimethoxybenzenepropanamine

HRID 2414816Notes

Reaction equation

HRID 2414816 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([NH2:15])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[H-]>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][NH2:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 8833563-(3,4-Dimethoxyphenyl)propanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 22810533,4-Dimethoxybenzenepropanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-(3,4-dimethoxy-phenyl)-propionamide (11.1 g, 53.0 mmol) in anhydrous THF (400 ml) is slowly added to a stirred, ice-cooled suspension of LiAlH4 (4.02 g, 106 mmol) in anhydrous THF (170 mL). Upon completion of the addition, the mixture is stirred at reflux for 2 h. After cooling to 0° C., H2O (5 mL) and NaOH 1N (5 mL) are added dropwise to decompose the excess of hydride. The suspension is filtered and evaporated. The residue is partitioned between H2O (40 mL) and CH2Cl2 (100 mL). The organic layer is washed with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure to give the title compound as a yellow oil.

Workup

  1. temperaturecooled
  2. additionUpon completion of the addition
  3. temperatureat reflux for 2 h
  4. filtrationThe suspension is filtered
  5. customevaporated
  6. customThe residue is partitioned between H2O (40 mL) and CH2Cl2 (100 mL)
  7. washThe organic layer is washed with saturated aqueous NaHCO3 and brine
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-579fd7996d074d99b24b95d096e3a580
Source dataset
uspto-grants-2004_11
Patent number
US06815451B2

Reaction notes

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