Hydrochloric Acid → 3-(2-Iodophenyl)-N-(2-phenylethyl)propanamide

HRID 2259220Notes

Reaction equation

HRID 2259220 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([OH:12])=O.[CH2:13]([NH2:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.Cl>C(Cl)Cl>[C:15]1([CH2:14][CH2:13][NH:21][C:10](=[O:12])[CH2:9][CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[I:1])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1001PhenethylamineHCID 27366673-(2-iodophenyl)propanoic Acid

Product 1

HCID 152835923-(2-Iodophenyl)-N-(2-phenylethyl)propanamideYield 120.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-iodobenzenepropionic acid (8 g, 0.029 mol) and phenethylamine (10.9 g, 0.090 mol) in methylene chloride (200 mL) was added N-ethyl-N-[3-(dimethylamino)propyl]carbodiimide hydrochloride (6.13 g, 0.032 mol) at room temperature. After 3 days, water (100 mL) and 2.5N HCl (50 mL) were added. The organic phase was separated, dried and concentrated to give an oil (13.3 g). The oil was chromatographed on silica gel and eluted with hexane: ethyl acetate (2:1) then hexane: ethyl acetate (1:1) to give a fraction containing a yellow solid 7.6 g (69%). Recrystallization from toluene (15 mL) and petroleum ether (150 mL) afforded 7.1 g of product, mp. 94.5°-95.5° C.

Workup

  1. customThe organic phase was separated
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-264580a40f8a43318e689a7f010a0c78
Source dataset
uspto-grants-1995_12
Patent number
US05472968

Reaction notes

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