Sodium Carbonate → (+/-)-1,3-dihydro-1-(1-{1-[1-(2-pyrazinyl)-1-ethyl]piperidin-4-yl}piperidin-4-yl)-2H-benzimidazol-2-one

HRID 2294938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2294938
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH:7]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1)[CH3:8].[O:16]=[C:17]1[N:21]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[C:20]2[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=2[NH:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>ClCCl.C(O)(=O)C.ClCCCl>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH:7]([N:9]1[CH2:14][CH2:13][CH:12]([N:25]2[CH2:24][CH2:23][CH:22]([N:21]3[C:20]4[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=4[NH:18][C:17]3=[O:16])[CH2:27][CH2:26]2)[CH2:11][CH2:10]1)[CH3:8]

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 5049666Sodium triacetoxyborohydrideHCID 214716861-(1-(2-Pyrazinyl)-ethyl)-4-oxopiperidine

Produkt 1

HCID 21471585(+/-)-1,3-dihydro-1-(1-{1-[1-(2-pyrazinyl)-1-ethyl]piperidin-4-yl}piperidin-4-yl)-2H-benzimidazol-2-oneAusbeute 47,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1-(1-(2-pyrazinyl)-ethyl)-4-oxopiperidine (37 mg), 4-(2-oxo-1-benzimidazolinyl)piperidine (41 mg), 1,2-dichloroethane (0.75 mL), glacial acetic acid (0.011 mL) and sodium triacetoxyborohydride (60 mg) was stirred at room temperature for 48 h. The reaction mixture was poured into dichloromethane (5 mL) and saturated aqueous Na2CO3 (3 mL) and the layers separated. The aqueous layer was extracted with dichloromethane (2×5 mL) and the combined organic layers dried over Na2SO4 and concentrated under reduced pressure. Purification by preparative TLC, eluting with chloroform; 10% methanol; 1% NH4OH, followed by trituration with diethyl ether gave 35 mg of (±)-1,3-dihydro-1-(1-{1-[1-(2-pyrazinyl)-1-ethyl]piperidin-4-yl}piperidin-4-yl)-2H-benzimidazol-2-one as a colorless solid: 1H NMR (400 MHz, CDCl3) 9.77 (br s, 1H), 8.69 (d, 1H), 8.54 (dd, 1H), 8.46 (d, 1H), 7.35 (m, 1H), 7.11-7.03 (m, 3H), 4.39 (m, 1H), 3.73 (q, 1H), 3.11 (m, 3H), 2.90 (m, 1H), 2.35-2.55 (m, 5H), 2.11 (m, 2H), 1.92-1.61 (m, 6H), 1.44 (d, 3H). Analysis calculated for C23H30N6O.0.1 H2O.0.3 CHCl3 : C: 63.01, H: 6.92, N: 18.92 found C: 63.07, H: 6.96, N: 18.76.

Aufarbeitung

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with dichloromethane (2×5 mL)
  3. dry with materialthe combined organic layers dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by preparative TLC
  6. washeluting with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-8a0575a1c8fd4fdc84ed6bb98f172348
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05691323

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