1,2-Dichloroethane → HCID 59347881, Verbindung

HRID 20840

Reaktionsgleichung

Reaktionsgleichung von HRID 20840
[CH3:1][C:2]([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[CH3:17])([CH3:11])[CH:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:18][C:19]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:18][C:19]1[C:27]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([NH:10][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:2]([CH3:1])([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[CH3:17])[CH3:11])=[O:22]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27366772-Chloro-3-(trifluoromethyl)benzoic acidHCID 59347786[2-Methyl-2-(2-methyl-1-pyrrolidinyl)-1-phenylpropyl]amine

Produkt 1

HCID 59347881HCID 59347881, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of [2-methyl-2-(2-methyl-1-pyrrolidinyl)-1-phenylpropyl]amine D26 (0.150 g; 0.647 mmol), 2-chloro-3-(trifluoromethyl)benzoic acid (0.174 g; 0.775 mmol), EDC (0.149 g; 0.777 mmol) and HOBt (0.020 g; 0.148 mmol) in DCM (4 ml) was shaken at room temperature for 66 hours. Saturated sodium hydrogen carbonate (8 ml) was added and shaking continued for 0.5 hours. The organic layer was passed through a phase separation cartridge and applied to a 2 g SCX column. The column was washed with DCM and methanol and the product eluted with 1M ammonia in methanol. The crude product was purified by chromatography on silica gel (20 g) eluting with 0-100% ethyl acetate in pentane gradient to afford the title compound as two pairs of enantiomers.

Aufarbeitung

  1. stirringshaking
  2. waitcontinued for 0.5 hours
  3. customThe organic layer was passed through a phase separation cartridge
  4. washThe column was washed with DCM and methanol
  5. washthe product eluted with 1M ammonia in methanol
  6. customThe crude product was purified by chromatography on silica gel (20 g)
  7. washeluting with 0-100% ethyl acetate in pentane gradient

Quellen und Nachweise

ORD-Eintrag
ord-d442d140b910474784016bfda8a268a9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745642B2

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