Sodium Bicarbonate → 4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbothioamide

HRID 272949

Reaktionsgleichung

Reaktionsgleichung von HRID 272949
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.P([O-])(OCC)(SCC)=[S:25].C([O-])(O)=O.[Na+]>ClCCl.O.C(OCC)(=O)C>[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22](=[S:25])[NH2:23])[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

7

Edukt 3

HCID 516892Sodium Bicarbonate2×HCID 53249491DiethyldithiophosphateHCID 598373944-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile

Produkt 1

HCID 866019004-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbothioamideAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

4-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-carbonitrile (2 g, 6.4 mmol), diethyl dithiophosphate (15 mL, 8.9 mmol), and water (1.5 mL) were combined and stirred at ambient temperature for 5 hours, 55° C. for 2 hours then 70° C. for 2 hours. The reaction mixture was diluted with dichloromethane (100 mL) and basified to pH 8 with a saturated solution of NaHCO3 in water, and solid NaHCO3. The layers were separated, and further dichloromethane (100 mL) was used to extract the product. The combined organics were dried using Na2SO4, filtered and concentrated in vacuo to leave a yellow oil. The compound was purified with column chromatography on 50 g of silica, eluting with dichloromethane:methanol:ammonia (96:4:0.4) to dichloromethane:methanol:ammonia (90:10:1) to give a clear oil. The clear oil was dissolved in ethyl acetate (150 mL) and washed with 10% Na2CO3 solution. The organic layer was dried using Na2SO4, filtered and concentrated in vacuo to give the title compound as a white solid (0.61 g, 28%).

Aufarbeitung

  1. wait70° C. for 2 hours
  2. customThe layers were separated
  3. extractionto extract the product
  4. customThe combined organics were dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto leave a yellow oil
  8. customThe compound was purified with column chromatography on 50 g of silica
  9. washeluting with dichloromethane:methanol:ammonia (96:4:0.4) to dichloromethane:methanol:ammonia (90:10:1)
  10. customto give a clear oil
  11. washwashed with 10% Na2CO3 solution
  12. customThe organic layer was dried
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5a70f34275684bb29dfa9b32eca1be85
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456164B2

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