Triethylamine → HCID 71612644, Verbindung

HRID 516811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516811
Cl.[NH2:2][CH2:3][CH:4]([OH:13])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[CH2:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[C:23]#[N:24])=[O:17].C(N(CC)CC)C>ClCCl>[OH:13][CH:4]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][NH:2][CH2:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[C:23]#[N:24])=[O:17]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27250721-Amino-3-phenoxypropan-2-ol hydrochlorideHCID 154801851-(2-Chloroacetyl)pyrrolidine-2-carbonitrile

Produkt 1

HCID 71612644HCID 71612644, VerbindungAusbeute 33,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1-amino-3-phenoxypropan-2-ol hydrochloride (7.9 g, 38.8 mmol) and 1-(2-chloroacetyl)pyrrolidine-2-carbonitrile (6.1 g, 35.3 mmol) in DCM (250 mL) was added triethylamine (15 mL, 106 mmol). The mixture was stirred at room temperature overnight. After the TLC showed that the reaction was complete, the mixture was washed by brine. The aqueous solution was extracted with dichloromethane (DCM) (3×100 mL) and the combined DCM solution was concentrated to give a crude product, which was purified by column chromatography to give 3.5 g of 1-(2-(2-hydroxy-3-phenoxypropylamino)acetyl)pyrrolidine-2-carbonitrile (as shown at 6). Yield was 33.6%.

Aufarbeitung

  1. washthe mixture was washed by brine
  2. extractionThe aqueous solution was extracted with dichloromethane (DCM) (3×100 mL)
  3. concentrationthe combined DCM solution was concentrated
  4. customto give a crude product, which
  5. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-79e546d14e7e495aa4b9737f448d38e1
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115082B2

Notizen zur Reaktion

Wird geladen…