Phenylacetyl chloride → HCID 21939585, Verbindung

HRID 1242791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1242791
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([N:17](C(C)C)CC)(C)C.[C:23]1([CH2:29][C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[C:1]([N:8]1[CH2:9][CH2:10][N:11]([NH:17][C:30](=[O:31])[CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

5

Edukt 3

HCID 7679Phenylacetyl chlorideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Produkt 1

HCID 21939585HCID 21939585, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

BOC-Piperazine (1.06 g) was combined with dichloromethane (20.0 mL) and diisopropylethylamine (1.49 mL). Phenylacetylchloride (0.90 mL) was added dropwise and the reaction was allowed to stir at room temperature for 24 hours. The reaction was then washed with HCl (1N in water, 3×5 mL), saturated aqueous sodium bicarbonate (3×5 mL) and brine (5 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated giving 1-BOC-4-phenylacetamidopiperazine (1.73 g). Yield=100% Step 2: The BOC group was removed from 1-BOC-4-phenylacetamidopiperazine according to example 137 giving phenylacetamidopiperazine hydrochloride. Yield=93%. Step 3: Phenylacetamidopiperazine hydrochloride was reacted with 8-ethyl-6-chloropurine (Example 140) according to Example 87. Yield=27%, ES-MS: (M+H)+ 351.

Aufarbeitung

  1. washThe reaction was then washed with HCl (1N in water, 3×5 mL), saturated aqueous sodium bicarbonate (3×5 mL) and brine (5 mL)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cb6d587a2c7d4577a0f3b334d7929e8c
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115741B2

Notizen zur Reaktion

Wird geladen…