HCID 19362820, compound → Phenyl acetate

HRID 1721015Notes

Reaction equation

HRID 1721015 reaction equation
[C:1]1([CH:7]([NH2:16])[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([O:20]CC)(=[O:19])[CH3:18].C(O)C>>[C:17]([O:20][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:19])[CH3:18].[C:1]1([CH:7]([NH2:16])[CH2:8][C:9]2[CH:10]=[CH:11][C:12]([Br:15])=[CH:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 19362820HCID 19362820, compoundHCID 21584252Ethanol ethylacetate2×

Product 2

HCID 31229Phenyl acetateHCID 19362820HCID 19362820, compound

Conditions

Temperature
60 °C

Procedure

1-Phenyl-2-(4-bromophenyl)ethylamine (6.71 gm, 2.43×10-2 mol) was dissolved in 40 ml of 25% ethyl acetate/ethanol. This solution was then added to a solution of S(-)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (5.69 gm, 2.43×10-2 mol) in 40 ml of 25% ethyl acetate/ethanol. The resulting solution was warmed to 60° C., and then allowed to stand at room temperature for 116 hours. The mixture was then left in a freezer for 24 hours. The resulting white precipitate was collected by vacuum filtration, washed with ethyl ether, and dried in vacuo to yield the desired (-) -α-methoxy-α-trifluoromethyl)phenyl acetate of (-)-1-phenyl-2-(4-bromophenyl)ethylamine (2.93 gm). The mother liquor was concentrated to dryness under reduced pressure, and the residue was crystallized as described above using 60 ml of 25% ethyl acetate/ethanol to yield an additional 0.63 gm of the phenylacetate of (-)-1-phenyl-2-(4-bromophenyl)ethylamine. The combined precipitates (3.56 gm, 57%, mp=143°-145° C.) were treated with 30 ml of 2.5N aqueous NaOH, extracted with three 30 ml portions of dichloromethane, and the combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator to yield the desired (-)-1-phenyl-2-(4-bromophenyl)ethylamine as a yellow oil (1.74 gm, 52%), [α]D25 =-62.7 (EtOH), shown to be 99.8% enantiomerically pure by chiral HPLC.

Workup

  1. waitThe mixture was then left in a freezer for 24 hours
  2. filtrationThe resulting white precipitate was collected by vacuum filtration
  3. washwashed with ethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-af6c767d705e4ca78e3f74dfe4e0973e
Source dataset
uspto-grants-1996_04
Patent number
US05508401

Reaction notes

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