Acrylonitrile → HCID 2502621, compound

HRID 526044Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[C:15](#[N:18])[CH:16]=[CH2:17]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:17][CH2:16][C:15]#[N:18])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 7855Acrylonitrile

HCID 2697221-(4-Methoxyphenyl)piperazine

Product 1

HCID 2502621HCID 2502621, compoundYield 74%

Procedure

4-Methoxyphenypiperazine (0.92 g, 4.68 mmol) and acrylonitrile (0.31 mL, 4.68 mmol) were mixed in a 10 mL reaction tube and stirred for 16 hours. The product was purified by silica gel flash chromatography (EtOAc/hexanes=1:8, Rf=0.3) to give 0.8 g (74%) white solid. 1H NMR (400 MHz, CDCl3) δ 6.98-6.90 (m, 2H), 6.90-6.82 (m, 2H), 3.79 (s, 3H), 3.17-3.07 (m, 4H), 2.78 (t, J=7.0 Hz, 2H), 2.74-2.64 (m, 4H), 2.57 (t, J=7.0 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ 154.0, 145.5, 118.8, 118.4, 114.5, 55.6, 53.4, 52.8, 50.6, 15.9. Upadhayaya, et al. (2004) Bioorg. Med. Chem. 12:2225-2238.

Workup

customThe product was purified by silica gel flash chromatography (EtOAc/hexanes=1:8, Rf=0.3)

Sources & evidence

ORD record: ord-3e8908d84a864bc99ee9e38c42110b90
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345703B2

Reaction notes

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