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

HRID 616255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 616255
[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-fa1a348aeef442a3ad441d1a35136e5f
Quelldatensatz
uspto-grants-1978_02
Patentnummer
US04073796

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