Ammonium Hydroxide → cis-2-Aminocyclohexanecarboxamide

HRID 7024

Reaktionsgleichung

Reaktionsgleichung von HRID 7024
C[O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@@H:6]1[NH2:11])=O.[OH-].[NH4+:13]>C1(C)C=CC=CC=1>[NH2:11][C@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C@H:5]1[C:3]([NH2:13])=[O:2]

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 24751169methyl (1R,2S)-2-aminocyclohexanecarboxylate

Produkt 1

HCID 2724813cis-2-Aminocyclohexanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

cis-2-Aminocyclohexanecarboxylic acid methyl ester (2.20 g, 14.0 mmol) was treated with aqueous ammonium hydroxide (40 mL) in toluene (40 mL) and stirred vigorously at room temperature for 16 h. The reaction was concentrated to dryness in vacuo and azeotroped with toluene (50 mL). The crude product, cis-2-aminocyclohexanecarboxylic acid amide, was used in the next reaction without purification: 1H NMR (400 MHz, DMSO-d6) δ 7.78 (2 H, s br), 7.67 (s, 1 H), 7.25 (s, 1 H), 1.87 (m, 2 H), 1.60 (m, 4 H), 1.41 (m, 4 H).

Aufarbeitung

  1. concentrationThe reaction was concentrated to dryness in vacuo
  2. customazeotroped with toluene (50 mL)
  3. customThe crude product, cis-2-aminocyclohexanecarboxylic acid amide, was used in the next reaction without purification

Quellen und Nachweise

ORD-Eintrag
ord-fc1c3c23629140928ac9e042705804cc
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084178B2

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