Hydrazine hydrate (1:1) → 4-((3-(3-Aminopropyl)phenylamino)methyl)heptan-4-ol

HRID 716777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716777
[OH:1][C:2]([CH2:28][CH2:29][CH3:30])([CH2:25][CH2:26][CH3:27])[CH2:3][NH:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][CH2:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH:8]=[CH:9][CH:10]=1.O.NN>C(O)C>[NH2:14][CH2:13][CH2:12][CH2:11][C:7]1[CH:6]=[C:5]([NH:4][CH2:3][C:2]([OH:1])([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])[CH:10]=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 672991752-(3-(3-(2-Hydroxy-2-propylpentylamino)phenyl)propyl)isoindoline-1,3-dione

Produkt 1

HCID 593170004-((3-(3-Aminopropyl)phenylamino)methyl)heptan-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(3-(3-(2-hydroxy-2-propylpentylamino)phenyl)propyl)isoindoline-1,3-dione (0.22 g, 0.71 mmol) and hydrazine hydrate (0.1 ml, 1.6 mmol) in ethanol was stirred at room temperature for 24 hours. The solvent was evaporated under reduced pressure. Purification by column chromatography (5% to 10% MeOH—CH2Cl2 gradient) gave 4-((3-(3-aminopropyl)phenylamino)methyl)heptan-4-ol as a light yellow semisolid. Yield (0.06 g, 18%); 1H NMR (400 MHz, DMSO-d6) δ 6.93 (t, J=7.6 Hz, 1H), 6.44-6.41 (m, 2H), 6.35 (d, J=7.6 Hz, 1H), 4.92 (t, J=5.2 Hz, 1H), 4.19 (bs, 1H), 2.87 (d, J=5.2 Hz, 2H), 2.54-2.50 (m, 2H), 2.44 (t, J=7.6 Hz, 2H), 1.55-1.62 (quintet, J=7.2 Hz, 2H), 1.42-1.33 (m, 4H), 1.32-1.27 (m, 4H), 0.85 (t, J=7.2 Hz, 6H); RP-HPLC (Method 3) tR=4.44 min, 97.48% (AUC); ESI MS m/z 279.31 [M+H]+.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customPurification by column chromatography (5% to 10% MeOH—CH2Cl2 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-446fe49112e54637b96a0f9d8cdf455b
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193669B2

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