1,2-Diphenylpropan-2-amine → HCID 131716146, compound

HRID 2351100Notes

Reaction equation

HRID 2351100 reaction equation
[C:1]1([CH2:7][C:8]([NH2:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[C:18]([C:26]([C:41]([OH:43])=[O:42])([OH:40])[C:27]([C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([OH:31])[C:28]([OH:30])=[O:29])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[C:32]([C:27]([C:28]([OH:30])=[O:29])([OH:31])[C:26]([C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([OH:40])[C:41]([OH:43])=[O:42])(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[C:1]1([CH2:7][C:8]([NH2:16])([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH3:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 1640871,2-Diphenylpropan-2-amineHCID 24820425HCID 24820425, compound

Product 1

HCID 131716146HCID 131716146, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Racemic 1,2-diphenyl-2-propylamine (86 g, 0.4 mol) was dissolved in 0.5 L 95% ethanol, heated to near reflux and added to a solution of (-)-dibenzoyltartaric acid monohydrate (151.9 g, 0.4 mol) in 0.5 L 95% ethanol also at reflux. A white solid crystallized immediately. The mixture was refluxed for 5 minutes, then allowed to cool to ambient temperature. The solid was collected by filtration and dried to give 86.2 g, [α]D =94.2° (C=0.5, CH3OH). The filtrate was saved. The solid was suspended in 0.9 L of 95% ethanol, stirred and heated to reflux for 1 hour, allowed to cool to ambient temperature and the white solid collected by filtration and vacuum dried at 80° C. for 8 hours to give 60.2 g of (-)-1,2-diphenyl-2-propylamine (-)-dibenzoyl tartrate, mp 194°-195° C. [α]D =-96.0° (C=0.5, CH3OH). 5.0 g of this salt was dissolved in 250 ml CHCl3 and 200 ml 5% NH4OH shaken vigorously, the layers separated and the organic phase washed with 3×200 ml 5% NH4OH, 2×200 ml H2O and dried over MgSO4. The solvent was evaporated to give 1.75 g of (-)-1,2-diphenyl-2-propylamine as an oil. The maleate salt was prepared by dissolving this oil in 25 ml of ethyl acetate and adding the solution to a hot solution of maleic acid (1.02 g, 8.87 mmol) in 50 ml of 3/1 ethyl acetate/isopropanol. Upon cooling a white solid crystallized, which was collected by filtration and vacuum dried to give 2.05 g of (-)-1,2-diphenyl-2-propylamine maleate, mp 176°-177° C., [α]D =-27.4° (C=1, CH3OH).

Workup

  1. temperatureheated
  2. temperatureto near reflux
  3. temperatureat reflux
  4. customA white solid crystallized immediately
  5. temperatureThe mixture was refluxed for 5 minutes
  6. filtrationThe solid was collected by filtration
  7. customdried
  8. customto give 86.2 g, [α]D =94.2° (C=0.5, CH3OH)
  9. temperatureheated
  10. temperatureto reflux for 1 hour
  11. temperatureto cool to ambient temperature
  12. filtrationthe white solid collected by filtration and vacuum
  13. customdried at 80° C. for 8 hours

Sources & evidence

ORD record
ord-3e1219c51e4a4b6a85b2520c839d2600
Source dataset
uspto-grants-1989_10
Patent number
US04871872

Reaction notes

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