Phenethylamine → HCID 4918878, compound

HRID 533369Notes

Reaction equation

HRID 533369 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=[O:15])[C:12]([OH:14])=O)=[CH:3]1.[CH2:16]([NH2:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC#N>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=[O:15])[C:12]([NH:24][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:14])=[CH:3]1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 4589028N-Methyl-3-indoleglyoxylic acid

Product 1

HCID 4918878HCID 4918878, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(1-Methyl-1H-indol-3-yl)-2-oxo-N-phenethyl-acetamide was synthesized following scheme II above starting from (1-methyl-1H-indol-3-yl)-oxo-acetic acid and phenethylamine. Yield (61%). HPLC ret. time 3.38 min, 10-99% CH3CN, 5 min run; 1H NMR (400 MHz, DMSO-d6) δ 8.80 (t, J=5.9 Hz, 1H), 8.73 (s, 1H), 8.25 (m, 1H), 7.60 (m, 1H), 7.36-7.20 (m, 7H), 3.91 (s, 3H), 3.47 (m, 2H), 2.86 (t, J=7.4 Hz, 2H); ESI-MS 307.3 m/z (MH+).

Workup

  1. customYield (61%)

Sources & evidence

ORD record
ord-3a624861957542b5a5e9c4781a7d3cf2
Source dataset
uspto-grants-2014_10
Patent number
US08853254B2

Reaction notes

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