Phenethylamine → N-(4-benzyloxy-3-fluorophenyl)-N'-(2-phenylethyl)ethanediamide

HRID 455828Notes

Reaction equation

HRID 455828 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O:12][C:13](=O)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:19]([F:31])[CH:18]=1)=[O:15])C>>[CH2:24]([O:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:14](=[O:15])[C:13]([NH:9][CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:12])=[CH:18][C:19]=1[F:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 1001PhenethylamineHCID 57810427Ethyl 2-((4-(benzyloxy)-3-fluorophenyl)amino)-2-oxoacetate

Product 1

HCID 57810151N-(4-benzyloxy-3-fluorophenyl)-N'-(2-phenylethyl)ethanediamideYield 99%

Procedure

Phenethyl-amine (33 mL, 520 mmol) was added to ethyl[(4-benzyloxy-3-fluorophenyl)amino](oxo)acetate (81 g, 260 mmol) and the mixture was sonicated at room temperature for 30 min. The resulting solid was filtered, washed with water and dried to give N-(4-benzyloxy-3-fluorophenyl)-N′-(2-phenylethyl)ethanediamide (100 g, 99%). 1H NMR (400 MHz, d6-DMSO): δ 10.72 (br s, 1H), 9.05 (m, 1H), 8.78 (m, 1H), 7.77 (m, 1H), 7.59 (m, 1H), 7.46-7.19 (m, 8H), 5.16 (m, 2H), 3.45 (m, 2H), 2.83 (m, 2H); IR (cm−1): 2980, 2883, 1653, 1522, 1506, 1441, 1385, 1221, 1122, 951, 808, 746, 696, 584; LC/MS (M+H=393).

Workup

  1. customthe mixture was sonicated at room temperature for 30 min
  2. filtrationThe resulting solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-0d7ea738d4694718a9a52583b8aa0ca9
Source dataset
uspto-grants-2013_07
Patent number
US08497284B2

Reaction notes

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