Phenethylamine → 2-(1H-indol-3-yl)-2-oxo-N-(2-phenylethyl)acetamide

HRID 533367Notes

Reaction equation

HRID 533367 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:14])[C:11](Cl)=[O:12])=[CH:2]1.[CH2:15]([NH2:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC#N>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:14])[C:11]([NH:23][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:12])=[CH:2]1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 899523-Indoleglyoxylyl chloride

Product 1

HCID 21767672-(1H-indol-3-yl)-2-oxo-N-(2-phenylethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(1H-Indol-3-yl)-2-oxo-N-phenethyl-acetamide was synthesized following scheme I above starting from (1H-indol-3-yl)-oxo-acetyl chloride and phenethylamine. Yield (61%). HPLC ret. time 3.17 min, 10-99% CH3CN, 5 min run; 1H NMR (400 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.79 (t, J=5.9 Hz, 1H), 8.67 (s, 1H), 8.23 (m, 1H), 7.53 (m, 1H), 7.33-7.19 (m, 7H), 3.47 (m, 2H), 2.85 (t, J=7.4 Hz, 2H); ESI-MS 293.3 m/z (MH+).

Workup

  1. customYield (61%)

Sources & evidence

ORD record
ord-33da839e7624485e8582a08c0cc4472c
Source dataset
uspto-grants-2014_10
Patent number
US08853254B2

Reaction notes

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