Acrylonitrile → 3-(4,4-Diphenylpiperidin-1-yl)propionitrile

HRID 394567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394567
Cl.[C:2]1([C:8]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:27](#[N:30])[CH:28]=[CH2:29]>>[C:2]1([C:8]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][CH2:10][N:11]([CH2:29][CH2:28][C:27]#[N:30])[CH2:12][CH2:13]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 30475044,4-Diphenylpiperidine hydrochloride

Produkt 1

HCID 155128643-(4,4-Diphenylpiperidin-1-yl)propionitrileAusbeute 87 %

Versuchsvorschrift

To a suspension of 4,4-diphenylpiperidine hydrochloride (195 mg, 0.712 mmol, 1.0 equiv) in ETOh (1.5 mL) was added triethylamine (0.25 mL, 1.83 mmol, 2.6 equiv) followed by acrylonitrile (0.13 mL, 2.01 mmol, 2.8 equiv). The resulting solution was stirred at room temperature under argon for 15 minutes and then concentrated. Water was added, and the mixture was extracted three times with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated to give 170 mg (87%) of tan solid, which was used for the next reaction without purification. m.p. 95-96° C.; 1H NMR (300 MHz, CDCl3) δ2.37 (m, 2H), 2,46 (m, 4H), 2.52 (m, 6H), 7.12 (m, 2H), 7.23 (m, 8H); 13C NMR (75 MHz, CDCl3) δ16.65, 36.71. 45.08, 50.78, 54.13, 119.70, 126.48, 127.78, 129.11, 147.87; IR (neat) 2944.4, 2821.0, 1495.5, 1445.9 cm−1.

Aufarbeitung

  1. concentrationconcentrated
  2. additionWater was added
  3. extractionthe mixture was extracted three times with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-53bcaf7e36bc4d7db3d3c736e5ccf75e
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602888B2

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