Triethylamine → 5-(1-(biphenyl-4-ylmethyl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1397896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397896
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12](=[O:14])[NH:13][C:9]=3[CH:8]=2)[CH2:3][CH2:2]1.[C:17]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19][CH:18]=1.CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CS(C)=O.C(OCC)(=O)C>[C:17]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:18]=[CH:19][C:20]([CH2:23][N:1]2[CH2:2][CH2:3][CH:4]([C:7]3[CH:16]=[CH:15][C:10]4[NH:11][C:12](=[O:14])[NH:13][C:9]=4[CH:8]=3)[CH2:5][CH2:6]2)=[CH:21][CH:22]=1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 824933395-(Piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Produkt 1

HCID 870562765-(1-(biphenyl-4-ylmethyl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-oneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A representative procedure for the synthesis of the piperidinyl aldehydes is the following. To a solution of compound 5 (0.15 g, 0.45 mmol) and biphenyl-4-carbaldehyde a (0.1 g, 0.55 mmol) in DMSO (2 mL) at 0° C. was added Et3N (0.13 mL, 0.97 mmol). After being stirred for 0.5 h at room temperature, NaBH(OAc)3 (0.11 g, 0.53 mmol) was added, and the mixture was stirred for 6 h. To the reaction mixture was added sat. NaHCO3 solution (10 mL), and the mixture was stirred for 15 min, followed by the addition of ethyl acetate (30 mL). The organic layer was separated and washed with sat. NaHCO3 and brine, and dried over Na2SO4 and evaporated. The light yellow solid was crystallized from diethyl ether to obtain the title compound 5a. Yield: 51%, off-white solid, mp>260° C. IR (KBr, cm−1) 3429 (CONH), 3055 (Ar—H), 2966 (Alph-H), 1703 (CO), 1620, 1518, 1422 (C—C), 1226 (C—N), 1145 (C-0); 1H NMR (500 MHz, DMSO d6) δ 1.62-1.71 (m, 4H, 2CH2), 2.04 (m, 2H, CH2), 2.48 (m, 1H, CH), 2.92 (m, 2H, CH2), 3.51 (s, 2H, NCH2), 6.77-6.81 (m, 3H, 3Ar—H), 7.32 (m, 1H, Ar—H), 7.40-7.45 (m, 4H, 4Ar—H), 7.59-7.64 (m, 4H, 4Ar—H), 10.43 (br. s, 1H, NH), 10.48 (br. s, 1H, NH), 13C NMR (125.7 MHz, DMSO d6) δ 33.64 (CH2), 41.86 (CH), 53.66 (CH2), 59.45 (NCH2), 106.91 (Ar—C), 108.42 (Ar—C), 118.99 (Ar—C), 126.56 (Ar—C), 126.66 (Ar—C), 127.42 (Ar—C), 127.98 (Ar—C), 129.03 (Ar—C), 129.06 (Ar—C), 129.63 (Ar—C), 138.92 (Ar—C), 140.11 (Ar—C), 155.59 (C═O). Anal. Calcd for C25H25N3O: C, 78.30; H, 6.57; N, 10.96%. Found: C, 78.22; H, 6.63; N, 10.86%.

Aufarbeitung

  1. stirringthe mixture was stirred for 6 h
  2. stirringthe mixture was stirred for 15 min
  3. customThe organic layer was separated
  4. washwashed with sat. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe light yellow solid was crystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-81482e04c45141f1becdd86e2c886c7c
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901304B1

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