Chloroacetyl chloride → (R)-2-chloro-N-[4-(3-dimethylaminopyrrolidin-1-yl)phenyl]acetamide

HRID 2426702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2426702
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][C@@H:17]([N:20]([CH3:22])[CH3:21])[CH2:16]2)=[CH:11][CH:10]=1.[Cl:23][CH2:24][C:25](Cl)=[O:26]>ClCCl>[Cl:23][CH2:24][C:25]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][C@@H:17]([N:20]([CH3:22])[CH3:21])[CH2:16]2)=[CH:11][CH:10]=1)=[O:26]

Komponenten

5

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 59815627[(R)-1-(4-aminophenyl)pyrrolidin-3-yl]dimethylamine

Produkt 1

HCID 67147914(R)-2-chloro-N-[4-(3-dimethylaminopyrrolidin-1-yl)phenyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Triethylamine (2.03 g) was added to a solution of (R)-[1-(4-aminophenyl)pyrrolidin-3-yl]-dimethylamine (3.15 g) in dichloromethane (120 ml), and then chloroacetyl chloride (2.26 g) was added dropwise. After 3 hours, the mixture was diluted with dichloromethane and washed with water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography (silica gel, eluent: methanol/dichloromethane). This resulted in the product with the molecular weight of 281.79 (C14H20CIN3O); MS (ESI): 282 (M+H+).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (silica gel, eluent: methanol/dichloromethane)
  6. customThis resulted in the product with the molecular weight of 281.79 (C14H20CIN3O)

Quellen und Nachweise

ORD-Eintrag
ord-5042bbeeb7df4e82b226ccdf7c55351d
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968550B2

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