Triethylamine → Tert-butyl 4-(4-amino-3-fluorobenzoyl)piperazine-1-carboxylate

HRID 408870

Reaktionsgleichung

Reaktionsgleichung von HRID 408870
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl.C(OCC)(=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)=[O:8])=[CH:4][C:3]=1[F:11]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 99714-Amino-3-fluorobenzoic acidHCID 111923Propylphosphonic anhydrideHCID 143452tert-Butyl piperazine-1-carboxylate

Produkt 1

HCID 58055815Tert-butyl 4-(4-amino-3-fluorobenzoyl)piperazine-1-carboxylateAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 4-amino-3-fluorobenzoic acid (4.97 g, 32.04 mmol), tert-butyl piperazine-1-carboxylate (5.97 g, 32.04 mmol) and triethylamine (10 mL) in dichloromethane (100 mL) was added 1-propanephosphonic acid cyclic anhydride (20 mL, 50% solution in ethyl acetate, dropwise). The reaction mixture was stirred for 1 hour then was diluted with ethyl acetate, washed with potassium carbonate (aqueous), dried (magnesium sulfate) and concentrated under reduced pressure to give the title compound (9.5 g). MS (ESI) m/z: 324.5 [M+H]+.

Aufarbeitung

  1. washwashed with potassium carbonate (aqueous)
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-64ce207decc04c1aa951166ab423390d
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759352B2

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