Water → 2-Benzyl-3-(dimethylamino)propan-1-ol

HRID 2309016Notes

Reaction equation

HRID 2309016 reaction equation
[CH2:1]([CH:8]([CH2:13][N:14]([CH3:16])[CH3:15])[C:9](OC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH2:1]([CH:8]([CH2:13][N:14]([CH3:16])[CH3:15])[CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 13653933Methyl 2-benzyl-3-dimethylaminopropionateHCID 21226445Aluminium lithium hydride

Product 1

HCID 136539342-Benzyl-3-(dimethylamino)propan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of methyl 2-benzyl-3-dimethylaminopropionate (60.0 g) in ether (300 ml) is added dropwise with stirring under a nitrogen atmosphere to a suspension of lithium aluminum hydride (28.0 g) in ether (700 ml). The reaction mixture is refluxed for 4 hours, then stirred at room temperature for 18 hours. The reaction mixture is cooled to 0°, and water (30 ml) is added cautiously (dropwise initially) followed by 10% NaOH (60 ml). The solid inorganic material is filtered off, and the filtrate dried over magnesium sulfate. The solvent is removed under reduced pressure to give 2-benzyl-3-dimethylaminopropanol as an oil which is used without further purification; NMR(CDCl3): δ7.12 (m, 5H), 5.62 (broad s, 1H), 3.57 (m, 2H).

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. temperatureThe reaction mixture is cooled to 0°
  3. filtrationThe solid inorganic material is filtered off
  4. dry with materialthe filtrate dried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-be0de0335ffa46bc987fc8355381d1a7
Source dataset
uspto-grants-1987_09
Patent number
US04692469

Reaction notes

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