1-Ethylpiperazine → HCID 59589361, compound

HRID 577202Notes

Reaction equation

HRID 577202 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.[CH2:10]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[CH3:11]>CN(C=O)C.O>[CH2:10]([N:12]1[CH2:17][CH2:16][N:15]([C:2]2[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=2)[CH2:14][CH2:13]1)[CH3:11]

Participants

4

Reactant 2

HCID 791961-EthylpiperazineHCID 27640536-Chloropyridine-3-carbaldehyde

Product 1

HCID 59589361HCID 59589361, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

6-chloropyridine-3-carbaldehyde (5.0 g, 35.32 mmol) and 1-ethylpiperazine (20.16 g, 176.60 mmol, 22.42 mL) were heated overnight in a mixture of DMF/water (1:1, 40 mL) at 100° C. The reaction mixture was extracted with ethyl acetate (2×100 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated to dryness to provide 6-(4-ethylpiperazin-1-yl)pyridine-3-carbaldehyde, which was used in the next reaction without any further purification (6.91 g, 89% yield); 1H NMR (400 MHz, DMSO-d6): δ 0.99 (t, 3H), 2.31 (q, 2H), 2.39 (m, 4H), 3.66 (m, 4H), 6.91 (d, J=9.2 Hz, 1H), 7.82 (d, J=9.2 Hz, 1H), 8.55 (s, 1H), 9.7 (s, 1H); LRMS (ES) m/z 219.8.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (2×100 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-80f7ff82125e469ab89ac44fcad8a8bb
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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