Chloroform → HCID 131716146, compound

HRID 728319Notes

Reaction equation

HRID 728319 reaction equation
C(Cl)(Cl)Cl.[NH4+:5].[OH-].O.[C:8]([C:16]([C:31]([OH:33])=[O:32])([OH:30])[C:17]([C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([OH:21])[C:18]([OH:20])=[O:19])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)C>[C:22]([C:17]([C:18]([OH:20])=[O:19])([OH:21])[C:16]([C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([OH:30])[C:31]([OH:33])=[O:32])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:23]1([CH2:22][C:17]([NH2:5])([C:16]2[CH:8]=[CH:9][CH:14]=[CH:13][CH:31]=2)[CH3:18])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14923Ammonium HydroxideHCID 24820425HCID 24820425, compound

Product 1

HCID 131716146HCID 131716146, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The filtrate residue which was saved in Illustration 4, was treated with 1 L CHCl3 and 0.9 L 5% NH4OH, shaken vigorously, the layers separated and the organic phase washed with 4×800 ml 5% NH4OH and 2×500 ml H2O, then dried over MgSO4 and evaporated to an oil 32.3 g, which is enriched in (+)-1,2-diphenyl-2-propylamine. This oil (32. 3 g, 0.153 mol) was dissolved in 200 ml hot 95% ethanol and added to a stirred solution of (+)-dibenzoyl tartaric acid monohydrate (57.55 g, 0.153 mol) in 600 ml of refluxing 95% ethanol. A white solid crystallized immediately, which was stirred at reflux for 5 minutes, then allowed to cool to ambient temperature. The solid was collected by filtration and vacuum dried at 80° C. for 8 hours to give 71.6 g of (+)-1,2-diphenyl-2-propylamine (+)-dibenzoyltartrate, mp 197°-198° C., [α]D =+95.8°, (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 and 2× 200 ml H2O 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 ethyl acetate and adding the solution to a hot solution of maleic acid (1.02 g, 8.78 mmol) in 50 ml 3/1 ethyl/acetate/isopropanol. Upon cooling a white solid crystallized, which was collected by filtration and vacuum dried to give 2.06 g of (+)-1,2-diphenyl-2-propylamine maleate, mp 177°-178° C., [α]D =+27.3° (C=1, CH3OH).

Workup

  1. customthe layers separated
  2. washthe organic phase washed with 4×800 ml 5% NH4OH and 2×500 ml H2O
  3. dry with materialdried over MgSO4
  4. customevaporated to an oil 32.3 g, which
  5. dissolutionThis oil (32. 3 g, 0.153 mol) was dissolved in 200 ml hot 95% ethanol
  6. customA white solid crystallized immediately
  7. stirringwhich was stirred
  8. temperatureat reflux for 5 minutes
  9. filtrationThe solid was collected by filtration and vacuum
  10. customdried at 80° C. for 8 hours

Sources & evidence

ORD record
ord-6f9daa73016345438fbab3d2dd4fc6c5
Source dataset
uspto-grants-1991_09
Patent number
US05047541

Reaction notes

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