Diethyl Ether → (+/-)-3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl)amino]propanenitrile

HRID 1941314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1941314
[OH-].C[N+:3](C)(C)[CH2:4][C:5]1C=CC=C[CH:6]=1.[C:13]1([CH2:19][NH:20][CH2:21][CH:22]2[CH2:27][CH2:26][C:25]3[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=3[O:23]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O(CC)CC>C(#N)C=C>[O:23]1[C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[CH2:26][CH2:27][CH:22]1[CH2:21][N:20]([CH2:19][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:6][CH2:5][C:4]#[N:3]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 66854Benzyltrimethylammonium hydroxideHCID 10753388Benzyl-chroman-2-ylmethyl-amine; oxalic acid

Produkt 1

HCID 18694181(+/-)-3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl)amino]propanenitrileAusbeute 28,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7855AcrylonitrileLösungsmittel

Versuchsvorschrift

3 ml of N,N,N-trimethylbenzenemethanaminium hydroxide was added dropwise to a stirred mixture of 60 g (±)-3,4-dihydro-N-(phenylmethyl)-2H-1-benzopyran-2-methanamine in 350 ml of 2-propenenitrile. After stirring for 4 days at reflux temperature, the reaction mixture was cooled and poured into 1,1'-oxybisethane. The whole was filtered over diatomaceous earth and the filtrate was evaporated, yielding 21 g (28.6%) of (±)-3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl)amino]propanenitrile as crude residue (interm. 21).

Aufarbeitung

  1. temperatureat reflux temperature
  2. temperaturethe reaction mixture was cooled
  3. filtrationThe whole was filtered over diatomaceous earth
  4. customthe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-632e59b94ee24eed8c75b30451580bfa
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05703115

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