Triethylamine → N-cyclopropyl-3,5-bis(3-methoxypropyl)benzamide

HRID 658251

Reaktionsgleichung

Reaktionsgleichung von HRID 658251
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[CH:14]=1)[C:9]([OH:11])=O.[CH:20]1([NH2:23])[CH2:22][CH2:21]1.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O>[CH:20]1([NH:23][C:9](=[O:11])[C:8]2[CH:12]=[C:13]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[CH:14]=[C:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=2)[CH2:22][CH2:21]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 574568723,5-Bis(3-methoxypropyl)benzoic acid

Produkt 1

HCID 57456873N-cyclopropyl-3,5-bis(3-methoxypropyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3,5-bis(3-methoxypropyl)benzoic acid (1 eq.) from the previous step in DCM (0.1 M) was added cyclopropanamine (1.3 eq.), o-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (aka. HATU, 1.5 eq.), and triethylamine (3 eq.). After stirring at rt for 18 h, the reaction was diluted with EtOAc. The organic extract was washed with 10% aqueous HCl solution, brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 50%→>70% EtOAc in Hex) to afford the title compound as an oil.

Aufarbeitung

  1. extractionThe organic extract
  2. washwas washed with 10% aqueous HCl solution, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography (SiO2, 50%→>70% EtOAc in Hex)

Quellen und Nachweise

ORD-Eintrag
ord-5e77c9af44c3494ebf888cf932c11eaf
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076359B2

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