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Water → Methyl 5-[4-(difluoromethoxy)phenyl]-1-[(1-oxidothiomorpholin-4-yl)carbonyl]piperidine-3-carboxylate

HRID 661224
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 661224
[F:1][CH:2]([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][NH:14][CH2:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]2)=[CH:6][CH:5]=1.C(N(CC)C(C)C)(C)C.[N:30]1([C:37](OC2C=CC([N+]([O-])=O)=CC=2)=[O:38])[CH2:35][CH2:34][S:33](=[O:36])[CH2:32][CH2:31]1.O>CN1CCCC1=O.C(OCC)(=O)C>[F:20][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:15][N:14]([C:37]([N:30]3[CH2:35][CH2:34][S:33](=[O:36])[CH2:32][CH2:31]3)=[O:38])[CH2:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]2)=[CH:8][CH:9]=1
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Komponenten

7

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 581165434-Nitrophenyl thiomorpholine-4-carboxylate 1-oxideHCID 58116573Methyl 5-[4-(difluoromethoxy)phenyl]piperidine-3-carboxylate

Produkt 1

HCID 58116576Methyl 5-[4-(difluoromethoxy)phenyl]-1-[(1-oxidothiomorpholin-4-yl)carbonyl]piperidine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

2.2 g (7.7 mmol) of methyl 5-[4-(difluoromethoxy)phenyl]piperidine-3-carboxylate were dissolved in 14 ml of N-methyl-2-pyrrolidone, and admixed with 4.0 ml (3.0 g, 23.0 mmol) of N,N-diisopropylethylamine and 3.3 g (11.5 mmol) of 4-nitrophenyl thiomorpholine-4-carboxylate 1-oxide. The reaction mixture was converted in the microwave at 180° C. for seven minutes. Subsequently, water and ethyl acetate were added, and the aqueous phase was removed and extracted repeatedly with ethyl acetate. The combined organic extracts were washed with water and saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by means of preparative HPLC. Yield: 2.2 g (59% of theory)

Aufarbeitung

  1. customthe aqueous phase was removed
  2. extractionextracted repeatedly with ethyl acetate
  3. washThe combined organic extracts were washed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by means of preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5791f84ae08842858779d0191f198d40
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08084469B2

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