Diethyl Ether → HCID 67199580, compound

HRID 240223Notes

Reaction equation

HRID 240223 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH2:16]([I:19])[CH2:17][CH3:18].C(OCC)C>C(#N)C>[I-:19].[CH3:1][N:2]([CH3:15])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][N+:12]([CH2:16][CH2:17][CH3:18])=[CH:13][CH:14]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 336431-IodopropaneHCID 227783Pyridine, 4-(4-dimethylaminophenyl)-

Product 1

HCID 67199580HCID 67199580, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-dimethyl-4-(pyridine-4-yl)aniline (0.2 g, 11 mmols) was dissolved in acetonitrile (50 ml) and propyl iodide (4 ml) was added. The mixture was heated at reflux for 4 hours then cooled to ambient temperature. Diethylether (50 ml) was added IDT322 (0.11 g, 2.9 mmols) crystallized upon standing and was removed via filtration. 1H NMR (DMSO-d6) δ 1.40 (t, 3H), 1.92 (q, 2H) 3.40 (s, 6H), 4.45 (t, 2H), 6.85 (t, 2H), 8.02 (d, 2H), 8.39 (d, 2H), 8.82 (d, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 hours
  3. customcrystallized
  4. customwas removed via filtration

Sources & evidence

ORD record
ord-ded5c7a8f51d471f9e679db7e6bd10f6
Source dataset
uspto-grants-2014_02
Patent number
US08647827B2

Reaction notes

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