Tetrahydrofuran → 4-(4-Morpholino-3-nitrophenyl)-4-(cyano)-4-(morpholino)-3-methylbutyronitrile

HRID 1249229

Reaktionsgleichung

Reaktionsgleichung von HRID 1249229
[C:1](#[N:5])/[CH:2]=[CH:3]/[CH3:4].O1CCCC1.[O:11]1[CH2:16][CH2:15][N:14]([CH:17]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[C:22]([N+:32]([O-:34])=[O:33])[CH:21]=2)[C:18]#[N:19])[CH2:13][CH2:12]1.[OH-].[K+]>O.CO>[O:29]1[CH2:30][CH2:31][N:26]([C:23]2[CH:24]=[CH:25][C:20]([C:17]([C:18]#[N:19])([N:14]3[CH2:15][CH2:16][O:11][CH2:12][CH2:13]3)[CH:3]([CH3:4])[CH2:2][C:1]#[N:5])=[CH:21][C:22]=2[N+:32]([O-:34])=[O:33])[CH2:27][CH2:28]1

Komponenten

7

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 14797Potassium HydroxideHCID 637921CrotononitrileHCID 21855724alpha-Morpholino-alpha(4-morpholino-3-nitrophenyl)-acetonitrile

Produkt 1

HCID 201649914-(4-Morpholino-3-nitrophenyl)-4-(cyano)-4-(morpholino)-3-methylbutyronitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 8.0 parts of crotononitrile in 20 parts by volume of tetrahydrofuran is added to a stirred mixture of 16.5 parts of α-morpholino-α(4-morpholino-3-nitrophenyl)-acetonitrile in 150 parts by volume of tetrahydrofuran and 1.5 parts of potassium hydroxide in 5 parts by volume of methanol at room temperature under an atmosphere of nitrogen. The reaction mixture is stirred for a further 6 hours, diluted with 500 parts by volume of water and extracted with 4×250 parts by volume of ethyl acetate. The combined organic extracts are dried over magnesium sulphate and concentrated under vacuum. The resulting crude product is triturated with a mixture of 50 parts by volume of ethyl acetate and hexane. The solid product is collected, washed with ethyl acetate and dried at 80° under vacuum to give 4-(4-morpholino-3-nitrophenyl)-4-(cyano)-4-(morpholino)-3-methylbutyronitrile having melting point 175°-177° C.

Aufarbeitung

  1. extractionextracted with 4×250 parts by volume of ethyl acetate
  2. dry with materialThe combined organic extracts are dried over magnesium sulphate
  3. concentrationconcentrated under vacuum
  4. customThe resulting crude product is triturated with a mixture of 50 parts by volume of ethyl acetate and hexane
  5. customThe solid product is collected
  6. washwashed with ethyl acetate
  7. customdried at 80° under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-833f64a256f84e5880a1459d0da9a247
Quelldatensatz
uspto-grants-1986_12
Patentnummer
US04629789

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