Sodium Hydroxide → 3-(2-Chloroethoxy)-N-(2-pyridylmethyl)propanamide

HRID 1774320

Reaktionsgleichung

Reaktionsgleichung von HRID 1774320
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH2:8].[OH-].[Na+].[Cl:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][C:17](Cl)=[O:18]>C(Cl)Cl>[Cl:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][C:17]([NH:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:18]

Komponenten

5

Edukt 3

HCID 14798Sodium Hydroxide2×HCID 195092-PyridinemethanamineHCID 860693723-(2-Chloroethoxy)propanoyl chloride

Produkt 1

HCID 867130993-(2-Chloroethoxy)-N-(2-pyridylmethyl)propanamideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A cooled solution of (2-pyridyl)methanamine (0.55 g, 5.1 mmol) in CH2Cl2 was stirred vigorously with 2% aqueous NaOH (12.2 mL, 6.1 mmol) while 3-(2-chloroethoxy)propanoyl chloride (6.1 mmol, prepared by refluxing 3-(2-chloroethoxy)propanoic acid with SOCl2) in CH2Cl2 was added dropwise. The same NaOH solution was then used to maintain pH at 9, and at costant pH the layers were separated. The organic phase was washed with 3 N HCl, with H2O, and then dried over Na2SO4 and evaporated under reduced pressure. The crude residue was chromatographed (CHCl3/AcOEt, 1:1, as eluent) to afford pure compound in 65% yield. 1H NMR (CDCl3): δ 2.38-2.41 (m, 2H), 2.60-2.63 (m, 2H), 3.54-3.60 (m, 2H), 3.66-3.69 (m, 2H), 4.45 (d, 2H, J=6.1 Hz), 6.12 (br t, 1H, D2O exchanged), 7.09-7.11 (m, 2H), 8.40-8.42 (m, 2H).

Aufarbeitung

  1. additionwas added dropwise
  2. temperatureto maintain pH at 9
  3. customat costant pH the layers were separated
  4. washThe organic phase was washed with 3 N HCl, with H2O
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude residue was chromatographed (CHCl3/AcOEt, 1:1, as eluent)
  8. customto afford pure compound in 65% yield

Quellen und Nachweise

ORD-Eintrag
ord-1a8c56e342884d0697e1ed2beba21371
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260400B2

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