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Formic Acid → (1-Methylpiperidin-4-yl)methyl 4-(4-chlorophenyl)piperazine-1-carboxylate

HRID 417952
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 417952
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:24](O)=O>C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=[O:15])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 284Formic AcidHCID 66651134(1-Piperidin-4-yl)methyl 4-(4-chlorophenyl)piperazine-1-carboxylate

Produkt 1

HCID 42635251(1-Methylpiperidin-4-yl)methyl 4-(4-chlorophenyl)piperazine-1-carboxylateAusbeute 30,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 712FormaldehydeLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

(1-piperidin-4-yl)methyl 4-(4-chlorophenyl)piperazine-1-carboxylate (4.07 g, 12.0 mmol) was dissolved in formic acid (20 mL) and 35% aqueous formaldehyde solution (20 mL). The reaction mixture was heated at 95° C. for 90 minutes, and then cooled to room temperature. The reaction mixture was quenched by slowly pouring it onto 1M aq Na2CO3 solution (200 mL), basified to pH10 with 1M aq KOH solution (30 mL) and extracted with DCM (3×100 mL). The combined organic layers were washed with brine (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by normal phase column chromatography (eluting with DCM, followed by a 97:2:1 mixture of DCM:MeOH:DIPEA) followed by reverse phase column chromatography (gradient eluting with MeOH in water, 0-80%) to give (1-methylpiperidin-4-yl)methyl 4-(4-chlorophenyl)piperazine-1-carboxylate (1.30 g, 30.7%) as a white solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe reaction mixture was quenched
  3. additionby slowly pouring it onto 1M aq Na2CO3 solution (200 mL)
  4. extractionextracted with DCM (3×100 mL)
  5. washThe combined organic layers were washed with brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by normal phase column chromatography (
  9. washeluting with DCM
  10. additionfollowed by a 97:2:1 mixture of DCM
  11. washMeOH:DIPEA) followed by reverse phase column chromatography (gradient eluting with MeOH in water, 0-80%)

Quellen und Nachweise

ORD-Eintrag
ord-ef0d73b334794f89a300092708a7999d
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08093248B2

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