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Methanol → N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(2-phenylethoxy)ethanamine hydrochloride

HRID 2209632
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2209632
[ClH:1].[CH2:2](N)[CH3:3].CC[N:7]([CH2:10][CH3:11])[CH2:8][CH3:9].[C:12]1([CH2:18][CH2:19][O:20][CH2:21][CH:22]=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:24]([BH3-])#[N:25].[Na+].[CH3:28][OH:29]>C1COCC1>[ClH:1].[O:29]1[C:28]2[CH:14]=[CH:15][CH:16]=[CH:9][C:8]=2[N:7]=[C:10]1[C:11]1[CH:3]=[CH:2][C:18]([CH2:19][O:20][CH2:21][CH2:24][NH:25][CH2:22][CH2:21][O:20][CH2:19][CH2:18][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:12][CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 887MethanolHCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 162493Acetaldehyde, 2-(2-phenylethoxy)-HCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 19420744N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(2-phenylethoxy)ethanamine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 2-[4-(benzoxazol-2-yl)benzyloxy)]ethylamine hydrochloride (0.11 g; 0.38 mmol) dissolved in MeOH (2 ml) and Et3N (0.053 ml; 0.38 mmol) is added dried and powdered 3 Å molecular sieves along with 2-phenylethoxyacetaldehyde (0.11 g; 0.68 mmol). After 1 hour, a 1M THF solution of sodium cyanoborohydride (0.75 ml; 0.75 mmol) is added dropwise. After 2 hours, the reaction mixture is quenched with acetone and 2N HCl and then concentrated in vacuo to dryness. The residue is dissolved in 3 ml 15% NaOH, extracted with Et2O 4×, dried (MgSO4) and concentrated in vacuo to dryness. The residue is purified by column chromatography using 10% MeOH/CH2Cl2. The product is dissolved in EtOH acidified with HCl/EtOH and concentrated to yield N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(2-phenylethoxy)ethanamine hydrochloride as a white solid. (m.p. 174°-175 ° C.).

Aufarbeitung

  1. customdried
  2. waitAfter 2 hours
  3. customthe reaction mixture is quenched with acetone and 2N HCl
  4. concentrationconcentrated in vacuo to dryness
  5. dissolutionThe residue is dissolved in 3 ml 15% NaOH
  6. extractionextracted with Et2O 4×
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo to dryness
  9. customThe residue is purified by column chromatography
  10. dissolutionThe product is dissolved in EtOH
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-50c20009f3104529bedb302b575df510
Quelldatensatz
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05455260

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