Water → HCID 131714673, compound

HRID 280296Notes

Reaction equation

HRID 280296 reaction equation
[CH3:1][N:2]([CH2:6][CH:7]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[C:3](=O)[CH3:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH3:1][N:2]([CH2:6][CH:7]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:8][S:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131714674HCID 131714674, compound

Product 1

HCID 131714673HCID 131714673, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of N-methyl-N-acetyl-2-benzyl-3-(4-methylthiophenoxy)propylamine (12.6 g) in dry ether (100 ml) is added dropwise to a stirred suspension of lithium aluminum hydride (4.0 g) in dry ether (250 ml). The reaction mixture is refluxed for 18 hours, and cooled to 0°. Water (3 ml) is added cautiously, followed by 15% sodium hydroxide (3 ml), and water (9 ml). The inorganic salts are filtered off, washed with ether (150 ml) and the combined ether solutions are dried over magnesium sulfate. The solvent is removed under reduced pressure to give N-methyl-N-ethyl-2-benzyl-3-(4-methylthiophenoxy)propylamine.

Workup

  1. temperatureThe reaction mixture is refluxed for 18 hours
  2. temperaturecooled to 0°
  3. filtrationThe inorganic salts are filtered off
  4. washwashed with ether (150 ml)
  5. dry with materialthe combined ether solutions are dried over magnesium sulfate
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-a908dbd8af8340ada03afa135a908669
Source dataset
uspto-grants-1986_05
Patent number
US04588746

Reaction notes

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