N-Methylbenzylamine → N-Benzyl-2-(1H-indol-3-yl)-N-methyl-2-oxo-acetamide

HRID 533371Notes

Reaction equation

HRID 533371 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]([NH:22][CH3:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC#N>[CH2:15]([N:22]([CH3:23])[C:11](=[O:12])[C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[O:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7669N-MethylbenzylamineHCID 899523-Indoleglyoxylyl chloride

Product 1

HCID 288389N-Benzyl-2-(1H-indol-3-yl)-N-methyl-2-oxo-acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Benzyl-2-(1H-indol-3-yl)-N-methyl-2-oxo-acetamide was synthesized following scheme I above starting from (1H-indol-3-yl)-oxo-acetyl chloride and benzyl-methyl-amine. Yield (54%). HPLC ret. time 2.96 min, 10-99% CH3CN, 5 min run; 1H NMR (400 MHz, DMSO-d6) δ 12.35 (s, 1H), 8.25 (s, 0.5H), 8.13-8.11 (m, 1.5H), 7.54 (m, 1H), 7.44-7.23 (m, 7H), 4.68 (s, 1H), 4.47 (s, 1H), 2.88 (s, 1.5H), 2.85 (s, 1.5H); ESI-MS 293.3 m/z (MH+).

Workup

  1. customYield (54%)

Sources & evidence

ORD record
ord-2054f56d00f946d3bbd83fc326022bf3
Source dataset
uspto-grants-2014_10
Patent number
US08853254B2

Reaction notes

Loading…