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1,2-Dichloroethane → Benzyl 4-(pyridin-4-ylcarbamoyl)piperidine-1-carboxylate

HRID 1351476
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1351476
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[N:24]1[CH:25]=[CH:26][C:21]([NH:20][C:17]([CH:14]2[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:16][CH2:15]2)=[O:19])=[CH:22][CH:23]=1
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Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 17274-AminopyridineHCID 181649HOAtHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Produkt 1

HCID 13937700Benzyl 4-(pyridin-4-ylcarbamoyl)piperidine-1-carboxylateAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

In DMF (5 mL), 1-[(benzyloxy)carbonyl]-4-piperidinecarboxylic acid (P. E. Maligres et al., Tetrahedron, 53:10983 (1997)) (1.00 g, 3.80 mmol), 4-aminopyridine (572 mg, 6.08 mmol), EDC (801 mg, 4.18 mmol), and HOAt (569 mg, 4.18 mmol) were combined and aged under N2 for 4 h. The reaction was partitioned between sat. NaHCO3 and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×). The combined organics were washed with water and brine then dried over Na2SO4, filtered and concentrated under reduced pressure, affording 1.16 g of benzyl 4-[(4-pyridinylamino)carbonyl]-1-piperidinecarboxylate as a yellow oil which was used without further purification.

Aufarbeitung

  1. customThe reaction was partitioned between sat. NaHCO3 and ethyl acetate
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×)
  4. washThe combined organics were washed with water and brine
  5. dry with materialthen dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-17fadbc7d3fa4a07b00e6cca4110f3d0
Quelldatensatz
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07217716B2

Notizen zur Reaktion

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