N,N-Dimethylethylenediamine → HCID 136593345, compound

HRID 1485908Notes

Reaction equation

HRID 1485908 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH:10]=O.[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][NH2:16]>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH:10]=[N:16][CH2:15][CH2:14][N:13]([CH3:17])[CH3:12]

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 96389Indole-2-carboxaldehyde

Product 1

HCID 136593345HCID 136593345, compoundYield 96.1%

Procedure

Replicate the preparation of the ligand used in Ex. 7 except use 0.200 g (1.378 mmol) of 1H-indole-2-carbaldehyde instead of pyrrole-2-carbaldehyde and use 0.158 mL (1.447 mmol) of the N1,N1-dimethylethane-1,2-diamine to give 0.285 g (96%) of N1-((1H-indol-2-yl)methylene)-N2,N2-dimethylethane-1,2-diamine as an off-white solid, which is analytically pure by GC-MS and 1H-NMR: 1H NMR (400 MHz, CDCl3) δ 9.11 (s, br, 1H), 8.19 (s, br, 1H), 7.53 (d, J=7.8 Hz, 1H), 7.23 (d, J=8.0 Hz, 1H), 7.14 (t, J=8.0 Hz, 1H), 7.00 (t, J=7.4 Hz, 1H), 6.65 (s, br, 1H), 3.64 (t, J=6.3 Hz, 2H), 2.53 (t, J=6.7 Hz, 2H), 2.22 (s, 6H).

Workup

  1. customthe preparation of the ligand

Sources & evidence

ORD record
ord-4a593deecdc54efd960c89d59db9ed90
Source dataset
uspto-grants-2016_08
Patent number
US09422375B2

Reaction notes

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