1-Naphthalenecarbonyl chloride → N-(1-Cyclohexylpyrrolidin-3-yl)naphthalene-1-carboxamide

HRID 1414881

Reaktionsgleichung

Reaktionsgleichung von HRID 1414881
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:3]1.[C:13]1([C:23](Cl)=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[CH:7]1([N:4]2[CH2:5][CH2:6][CH:2]([NH:1][C:23]([C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)=[O:24])[CH2:3]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Komponenten

4

Edukt 2

HCID 701461-Naphthalenecarbonyl chlorideHCID 36700741-Cyclohexylpyrrolidin-3-amine

Produkt 1

HCID 20355413N-(1-Cyclohexylpyrrolidin-3-yl)naphthalene-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To 9.69 gm. (0.06 mole) of 3-amino-1-cyclohexylpyrrolidine in 50 ml. of chloroform was added dropwise a solution of 8.4 gm. (0.046 mole) of 1-naphthalenecarbonyl chloride in 50 ml. of chloroform. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate containing 10% isopropyl ether and dilute hydrochloric acid. The separated acid layer was made basic with dilute sodium hydroxide solution and extracted with chloroform. The chloroform solution was dried over sodium sulfate, concentrated and the residue crystallized from ethyl acetate. The product weighed 3.8 gm. (25%) and melted at 119°-120° C.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate containing 10% isopropyl ether and dilute hydrochloric acid
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform solution was dried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a39babad78914383bef9c45d056ae6e9
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04002757

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