Sulfuric Acid → alpha,alpha-Diphenyl-1-phenylmethyl-3-pyrrolidineacetamide

HRID 1193500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1193500
S(=O)(=O)(O)O.[CH2:6]([N:13]1[CH2:17][CH2:16][CH:15]([C:18]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:19]#[N:20])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-:33].[Na+]>C(Cl)(Cl)Cl>[C:21]1([C:18]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([CH:15]2[CH2:16][CH2:17][N:13]([CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:14]2)[C:19]([NH2:20])=[O:33])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 13633740alpha-(1-Benzyl-3-pyrrolidinyl)-alpha,alpha-diphenylacetonitrile

Produkt 1

HCID 13633759alpha,alpha-Diphenyl-1-phenylmethyl-3-pyrrolidineacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To 250 ml of concentrated sulfuric acid under agitation was added, slowly at 70° C., 170 g (0.48 mole) of α-(1-benzyl-3-pyrrolidinyl)-α,α-diphenylacetonitrile. Stirring was continued for 16 hr at 75°-80° C. The solution was cooled and poured into a mixture of ice, 50% sodium hydroxide solution and chloroform. The chloroform layer was separated and the aqueous phase extracted three more times with chloroform. The combined chloroform layers were dried and concentrated in vacuo to give 188 g of residual oil. A portion of the oil was crystallized in isopropanol and the solid recrystallized from a mix of isopropanol and isopropyl ether to give a light brown solid, m.p. 135°-138° C.

Aufarbeitung

  1. temperatureThe solution was cooled
  2. customThe chloroform layer was separated
  3. extractionthe aqueous phase extracted three more times with chloroform
  4. dry with materialThe combined chloroform layers were dried
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d20f6895455e4f0287c92a09cbfd6ed2
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04810703

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