Methanol → 1-Phenethylamine

HRID 377317Notes

Reaction equation

HRID 377317 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:7]([O:10]CC)(=[O:9])[CH3:8].[C:13]1([CH:19]([NH2:21])[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:22][OH:23]>>[CH3:22][O:23][C:3]1[CH:2]=[C:1]([CH:6]=[CH:5][CH:4]=1)[CH2:13][C@H:14]1[C:8]([C:7]([OH:10])=[O:9])=[CH:17][CH2:16][CH2:15]1.[C:13]1([CH:19]([NH2:21])[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 74081-PhenethylamineHCID 8058HexaneHCID 8857Ethyl Acetate

Product 2

HCID 74081-PhenethylamineHCID 54280380HCID 54280380, compound

Procedure

To a n-hexane and ethyl acetate solution (80 ml, 1:1) of the crude carboxylic acid was added (+)-1-phenylethylamine (1.96 g) with stirring at the room temperature. A precipitated colorless powder (3.97 g, mp : 125-131° C.) was collected by filtration and the additional powder (0.20 g, mp : 127-129° C.) was obtained from the filtrate Recrystallization of the combined powder from n-hexane--ethyl acetate (1:1, 100 ml) afforded a pure salt of (-)-5(S)-(3-methoxybenzyl)-1-cyclopentenecarboxylic acid and (+)-1-phenylethylamine as a colorless needles (3.27 g, mp : 135-136° C., [α]D : -21.87° (C=1, MeOH)).

Workup

  1. filtrationA precipitated colorless powder (3.97 g, mp : 125-131° C.) was collected by filtration
  2. customthe additional powder (0.20 g, mp : 127-129° C.) was obtained from the filtrate Recrystallization of the combined powder from n-hexane--ethyl acetate (1:1, 100 ml)

Sources & evidence

ORD record
ord-0238000ed16a445694c118cc6d7ceba0
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

Loading…