Piperidine → HCID 9968042, Verbindung

HRID 1828563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1828563
[C:1]1([C:7]2[N:8]=[C:9]([C:19](O)=[O:20])[N:10]([CH3:18])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(Cl)Cl.O>[N:23]1([NH:22][C:19]([C:9]2[N:10]([CH3:18])[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)=[O:20])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[N:29]1([C:19]([C:9]2[N:10]([CH3:18])[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)=[O:20])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Komponenten

9

Edukt 5

HCID 8082PiperidineHCID 166581-AminopiperidineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 22066062HCID 22066062, Verbindung

Produkt 2

HCID 9968042HCID 9968042, VerbindungHCID 10155451HCID 10155451, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4,5-diphenyl-I-methylimidazole-2-carboxylic acid (50 mg, 0.18 mmol) from Step A, 1-aminopiperidine (0.052 mL, 0.36 mmol) (containing a small percent of piperidine as an impurity), PyBOP (NovaChem) (140 mg, 0.2 mmol) and N,N-diisopropyl-N-ethylamine (DIPEA) (0.065 mL, 0.2 mmol) in methylene chloride (2 mL) was stirred at rt for 20 hr. The reaction was diluted with water and extracted twice with methylene chloride. The organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified twice by prep TLC (1 mm, silica gel) eluting with 5% methylene chloride, 35% ethyl acetate in hexanes to afford the primary product N-(piperidin-1-yl)-4,5-diphenyl-1-methylimidazole-2-carboxamide and 2-(piperidin-1-ylcarbonyl)-4,5-diphenyl-1-methylimidazole as a byproduct. HPLC/MS: 361 (M+1); Rt=2.64 min; 1HNMR (CDCl3): 1.4–1.7 (m, 2H), 1.92 (m, 4H), 2.96 (br s, 4H), 3.90 (s, 3H), 7.24 (m, 3H), 7.34 (m, 2H), 7.50 (m, 5H).

Aufarbeitung

  1. extractionextracted twice with methylene chloride
  2. washThe organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified twice by prep TLC (1 mm, silica gel)
  6. washeluting with 5% methylene chloride, 35% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-aebc1b1aa1984c5589c294f7bc3adf94
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07057051B2

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