Pyridine → N-(cyclohexylmethyl)-N-methylcarbamoyl chloride

HRID 1158422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158422
[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1.[CH:19]1([CH2:25][NH:26][CH3:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C(Cl)Cl>[CH:19]1([CH2:25][N:26]([CH3:27])[C:2]([Cl:1])=[O:4])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 117276(Cyclohexylmethyl)(methyl)amine

Produkt 1

HCID 59512492N-(cyclohexylmethyl)-N-methylcarbamoyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of triphosgene (77 mg, 0.259 mmol) in CH2Cl2 (1 mL) at −78° C. is added dropwise pyridine (63 μl, 0.786 mmol) followed by a solution of cyclohexylmethyl-methylamine (100 mg, 0.786 mmol) in CH2Cl2 (1 mL). The yellow mixture is allowed to reach RT and stirred overnight. The solvent is concentrated, and the residue taken up in AcOEt. An aqueous saturated solution of NaHCO3 is added, the layers are separated and the aqueous one is extracted twice with AcOEt. The combined organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound as a yellow oil. TLC, Rf (CH2Cl2/MeOH 95:5)=0.95. MS (LC-MS): 189.1 [M+H]+.

Aufarbeitung

  1. customto reach RT
  2. concentrationThe solvent is concentrated
  3. additionAn aqueous saturated solution of NaHCO3 is added
  4. customthe layers are separated
  5. extractionthe aqueous one is extracted twice with AcOEt
  6. washThe combined organic extracts are washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-96ee158291064cb79fc0ca6561eeabc2
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807709B2

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