Benzoic acid, 4-fluoro-, ethyl ester → 4-Benzylbenzoate piperidine 4-ethyl benzoate

HRID 2190555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190555
[CH2:1]([O:8][C:9](=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20]NCC2)=[CH:12][CH:11]=1)[C:2]1C=CC=CC=1.C([O:25][C:26](=[O:34])[C:27]1[CH:32]=[CH:31][C:30](F)=[CH:29][CH:28]=1)C.C(N(C(C)C)CC)(C)C>CN(C1C=CN=CC=1)C.CS(C)=O>[CH2:26]([C:13]1[CH:12]=[CH:11][C:10]([C:9]([O-:8])=[O:22])=[CH:15][CH:14]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[NH:16]1[CH2:13][CH2:14][CH2:15][CH2:20][CH2:21]1.[CH3:1][CH2:2][C:30]1[CH:29]=[CH:28][C:27]([C:26]([OH:25])=[O:34])=[CH:32][CH:31]=1

Komponenten

6

Edukt 3

HCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 81531DiisopropylethylamineHCID 539216634-Piperazin-1-yl-benzoic acid benzyl ester

Produkt 1

HCID 1317300884-Benzylbenzoate piperidine 4-ethyl benzoateAusbeute 128 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 4-piperazin-1-yl-benzoic acid benzyl ester (500 mg, 1.68 mmol), 4-fluoro benzoic acid ethyl ester (1.4 g, 8.4 mmol), diisopropylethyl amine (1.47 mL, 8.4 mmol) and a catalytic amount of DMAP in DMSO (6 mL) was stirred at 130° C. in a sealed tube for 70 h. The mixture was the cooled partitioned between EtOAc and water. The EtOAc layer was collected, dried over Na2SO4, filtered and concentrated. The residue was suspended in hexanes and the suspension was then filtered. The solid obtained passed through a plug of silica gel using 0-100% EtOAc in hexanes to afford the product (480 mg, Yield; 64%). HRMS m/z calcd for C27H28N2O4 [M+H]+: 445.2122; Found: 445.2120.

Aufarbeitung

  1. custompartitioned between EtOAc and water
  2. customThe EtOAc layer was collected
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationthe suspension was then filtered
  7. customThe solid obtained

Quellen und Nachweise

ORD-Eintrag
ord-965bb96018b546ef8eeba852a2b0688a
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324385B2

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