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Formaldehyde → 7-(4-Phenyl-1-piperidinyl)-3-[(4-phenyl-1-piperidinyl)methyl]-1,2,4-triazolo[4,3-a]pyridine-8-carbonitrile

HRID 1428518
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1428518
[C:1]([C:3]1[C:4]2[N:5]([CH:21]=[N:22][N:23]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)#[N:2].[C:24]1([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH2:36]=O>C(O)(=O)C.C(Cl)Cl>[C:15]1([CH:12]2[CH2:13][CH2:14][N:9]([C:8]3[CH:7]=[CH:6][N:5]4[C:21]([CH2:36][N:33]5[CH2:32][CH2:31][CH:30]([C:24]6[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=6)[CH2:35][CH2:34]5)=[N:22][N:23]=[C:4]4[C:3]=3[C:1]#[N:2])[CH2:10][CH2:11]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 698734-PhenylpiperidineHCID 667888318-Cyano-7-(4-phenylpiperidinyl)[1,2,4]triazolo[4,3-a]pyridine

Produkt 1

HCID 574594867-(4-Phenyl-1-piperidinyl)-3-[(4-phenyl-1-piperidinyl)methyl]-1,2,4-triazolo[4,3-a]pyridine-8-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of D8 (0.301 g, 0.992 mmol) in acetic acid (4.5 ml) were added 4-phenylpiperidine (0.160 g, 0.992 mmol) and formaldehyde (0.223 ml, 0.992 mmol; 37%). The resulting mixture was heated in a sealed tube at 80° C. for 16 h. The reaction mixture was diluted with DCM and washed with 2M NaOH. The organic layer was separated, dried (MgSO4) and concentrated in vacuo. The crude product thus obtained was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2% as eluent). The desired fractions were collected and concentrated in vacuo to yield a residue that was purified by HPLC (C18Xbridge 19×100; mobile phase AcONH4/CH3CN gradient as eluent). The desired fractions were collected and concentrated in vacuo to yield final compound E12 (0.085 g, 18%).

Aufarbeitung

  1. washwashed with 2M NaOH
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product thus obtained
  6. customwas purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2% as eluent)
  7. customThe desired fractions were collected
  8. concentrationconcentrated in vacuo
  9. customto yield a residue that
  10. customwas purified by HPLC (C18Xbridge 19×100; mobile phase AcONH4/CH3CN gradient as eluent)
  11. customThe desired fractions were collected
  12. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6acb05c7c1c94964b57625ec041effd9
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08937060B2

Notizen zur Reaktion

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