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

HRID 382659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 382659
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.CCN(CC)CC.[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 Et3N (0.25 mL, 1.8 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 characterized spectroscopically and used for the next reaction without purification.

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-21816d2b024c4b72a4b04188ccba41fd
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310076B1

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