Sodium ethoxide → 4-[2-(1-Ethyl-4,5-dihydro-imidazol-2-yl)ethyl]-pyridine

HRID 485809

Reaction equation

[C:1]([CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)#N.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:22]([NH:24][CH2:25][CH2:26][NH2:27])[CH3:23].[O-]CC.[Na+]>C(O)C>[CH2:22]([N:24]1[CH2:25][CH2:26][N:27]=[C:1]1[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)[CH3:23]

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of 4-(2-cyanoethyl)pyridine (1.32 g, 0.01M) and N-ethyl-1,2-diaminoethane mono-p-toluenesulfonate (5.5 g, 0.02M) were heated at 190° C. for 4 hrs under nitrogen. The reaction mixture was dissolved in ethanol (30 ml) and sodium ethoxide (0.02M) in ethanol (50 ml) was added. The mixture was filtered and the filtrate was stripped to dryness and distilled at 130° C./0.2 mmHg to yield 4-[2-(1-ethyl-4,5-dihydro-imidazol-2-yl)ethyl]-pyridine (1.2 g, 60% yield).

Workup

filtrationThe mixture was filtered
distillationdistilled at 130° C./0.2 mmHg

Sources & evidence

ORD record: ord-4c2555b3c17d415e93a0b6b88e44caf0
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04537969

Linked notes

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