Dichloromethane → {4-[4-(4-Aminobutyl)phenyl]butyl}carbamic acid benzyl ester

HRID 1696851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696851
[CH2:1]([O:8][C:9](=[O:36])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.C(Cl)Cl>C(O)C>[CH2:1]([O:8][C:9](=[O:36])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])=[CH:17][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 9321HydrazineHCID 66860915(4-{4-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyl]phenyl}butyl)carbamic acid benzyl ester

Produkt 1

HCID 58100085{4-[4-(4-Aminobutyl)phenyl]butyl}carbamic acid benzyl esterAusbeute 206,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution containing 59 (4.0 g, 8.20 mmol) and hydrazine (2.06 g, 41.20 mmol) dissolved in ethanol (50 mL) and methylene chloride (10 mL) was heated to reflux. The reaction mixture was allowed to stir for 16 h under N2 atmosphere. The solution was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol) and dichloromethane to afford the desired product 7 (6.00 g, 72%) as an off white solid: 1H NMR (300 MHz, CDCl3) δ 7.34 (s, 4H), 7.07 (s, 4H), 5.08 (s, 2H), 3.18 (t, 2H), 2.94 (s, 2H), 2.70 (t, 2H), 2.59 (t, 4H), 1.65-1.47 (m, 5H); m/z (ESI) 355 [C22H30N2O2+H]+.

Aufarbeitung

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting residue was purified by column chromatography
  4. washeluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol) and dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-6707dc3f65424cb5b3195ce19164ad24
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163758B2

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