Triethylamine → (+)-4-{4-[3-(3-Benzo[1,3]dioxol-5-ylmethyl-piperidin-1-yl)-propionyl]-piperazin-1-yl}-2-fluoro-benzonitrile

HRID 2354561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354561
[C:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([F:19])[CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])[CH:2]=[CH2:3].[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][NH:32][CH2:31]3)=[CH:28][C:23]=2[O:22][CH2:21]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][N:32]([CH2:3][CH2:2][C:1]([N:5]4[CH2:6][CH2:7][N:8]([C:11]5[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([F:19])[CH:12]=5)[CH2:9][CH2:10]4)=[O:4])[CH2:31]3)=[CH:28][C:23]=2[O:22][CH2:21]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 170395273-Benzo[1,3]dioxol-5-ylmethyl-piperidineHCID 684518974-(4-Acryloylpiperazin-1-yl)-2-fluorobenzonitrile

Produkt 1

HCID 12000651(+)-4-{4-[3-(3-Benzo[1,3]dioxol-5-ylmethyl-piperidin-1-yl)-propionyl]-piperazin-1-yl}-2-fluoro-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-(4-acryloyl-piperazin-1-yl)-2-fluoro-benzonitrile (0.125 g, 0.48 mmol), (+)-3-benzo[1,3]dioxol-5-ylmethyl-piperidine (0.106 g, 0.48 mmol) and triethylamine (0.088 ml, 0.629 ml) in THF (1.6 ml) is stirred at rt for 25 h. The mixture is diluted with CH2Cl2 and washed with sat. aq. Na2CO3 solution The organic layer is separated off, dried over Na2SO4 and evaporated. The residue is purified by MPLC (60 g silica gel, eluent CH2Cl2:MeOH 9:1) to give the title compound, (+)-4-{4-[3-(3-benzo[1,3]dioxol-5-ylmethyl-piperidin-1-yl)-propionyl]-piperazin-1-yl}-2-fluoro-benzonitrile, as a colourless foam:

Aufarbeitung

  1. washwashed with sat. aq. Na2CO3 solution The organic layer
  2. customis separated off
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue is purified by MPLC (60 g silica gel, eluent CH2Cl2:MeOH 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-70f296480ab64e799f1e9dcefb154d27
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754719B2

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