Water → 1,2-Diphenylethyl-N-methylamine

HRID 2351104Notes

Reaction equation

HRID 2351104 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([NH:12][CH:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(OCC)=O.O.[OH-].[Na+]>O1CCCC1>[CH3:7][NH:12][CH:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 234956Ethyl (1,2-diphenylethyl)carbamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 1109861,2-Diphenylethyl-N-methylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of lithium aluminum hydride (12.4 g, 0.032 mol) in 300 ml of tetrahydrofuran at 0° C. under nitrogen was added dropwise a solution of N-carboethoxy-1,2-diphenylethylamine (35.0 g, 0.13 mmol) in 200 ml of tetrahydrofuran. The mixture was heated to reflux for 8 hours. The mixture was cooled in an ice-water bath and water (13 ml), 15% NaOH (13 ml) and water (39 ml) were carefully added to the mixture. The mixture was warmed to ambient temperature and the precipitated salts were removed by filtration through celite. Removal of solvent gave N-methyl-1,2-diphenylethylamine, 26.8 g as a colorless oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 hours
  3. temperatureThe mixture was cooled in an ice-water bath
  4. customthe precipitated salts were removed by filtration through celite
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-5673fd23e0e94d79b64e16e290f58ad5
Source dataset
uspto-grants-1989_10
Patent number
US04871872

Reaction notes

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