Hydrochloric Acid → 3-Phenylbutylamine

HRID 566698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566698
[C:1]1([CH:7]([CH3:11])[CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:18].[Na+].Cl>CO>[C:1]1([CH:7]([CH3:11])[CH2:8][CH2:9][NH2:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 859793-PhenylbutanalHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 30159623-Phenylbutylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3-phenylbutyraldehyde (3 ml, 20.18 mmol), ammonium acetate (15 g, 195 mmol) and sodium cyanoborohydride (900 mg, 14.32 mmol) in methanol (50 ml) was stirred overnight under an argon atmosphere. The reaction was acidified to pH 2 by the addition of conc HCl. The solvent was evaporated, dichloromethane and water were added, and the aqueous layer was made basic (pH 12) by the addition of solid potassium hydroxide. Extraction (dichloromethane) and concentration gave the title compound as an oil. ES-MS (m/z): 150.2 (M+H)+; 1H NMR (CDCl3): d 7.40-7.17 (m, 5H, Ph), 2.81 (q, 1H, CH), 2.62 (m, 2H, CH2), 1.76 (dq, 2H, CH2), 1.29 (d, 3H, CH3).

Aufarbeitung

  1. customThe solvent was evaporated
  2. additiondichloromethane and water were added
  3. additionby the addition of solid potassium hydroxide
  4. extractionExtraction (dichloromethane) and concentration

Quellen und Nachweise

ORD-Eintrag
ord-d58acd70c4024256abfb60e0d7f8474b
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06174901B1

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