Chloroform → HCID 131716146, compound

HRID 2351101Notes

Reaction equation

HRID 2351101 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 702EthanolSolvent2×

Procedure

The filtrate residue which was saved in Illustration 3, 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 use 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 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 ethyl acetate and adding the solution to a hot solution of maleic acid (1.02 g, 8.78 mmole) 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. customA white solid crystallized immediately
  6. stirringwhich was stirred
  7. temperatureat reflux for 5 minutes
  8. filtrationThe solid was collected by filtration and vacuum
  9. customdried at 80° C. for 8 hours

Sources & evidence

ORD record
ord-2735e4d80e16496cbfc6357d656067b1
Source dataset
uspto-grants-1989_10
Patent number
US04871872

Reaction notes

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