Potassium Carbonate → 4-[(10-benzyl-9,10-diazatricyclo-[4.2.1.12,5]dec-9-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide

HRID 1912342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912342
[CH2:1]([N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH:10]1[NH:17][CH:13]2[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:19]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=1)[C:20]1[CH:32]=[CH:31][C:23]([C:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]1[CH:9]2[CH:10]3[N:17]([CH:19]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=4)[C:20]4[CH:32]=[CH:31][C:23]([C:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=4)[CH:13]([CH:14]1[CH2:15][CH2:16]2)[CH2:12][CH2:11]3)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 99968274-[(Chloro)(3-methoxyphenyl)methyl]-N,N-diethylbenzamideHCID 508962899-Benzyl-9,10-diazatricyclo[4.2.1.12,5]decane

Produkt 1

HCID 672383574-[(10-benzyl-9,10-diazatricyclo-[4.2.1.12,5]dec-9-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamideAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture formed of 9-benzyl-9,10-diazatricyclo[4.2.1.12,5]decane prepared in Example 2.1 (2.19 mmoles), 4-[chloro-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide obtained in Example 3.1 (1.5 equivalents), anhydrous potassium carbonate (3 equivalents) and acetonitrile (20 ml), is heated at reflux for 3 days. At the end the mixture was filtered under vacuum and the liquid phase recovered. The solvent was evaporated under vacuum and the residual oil purified by flash chromatography. The eluent was ligroin/ethyl acetate 7/3 (v/v). The compound 4-[(10-benzyl-9,10-diazatricyclo-[4.2.1.12,5]dec-9-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide was obtained. Yield: 52%. IR (nujol) (λ=cm−1) 1680 (C═O); 1H-NMR (CDCl3) δ 1.00-1.30 (m, 6H); 1.60-2.20 (m, 8H); 2.75-2.85 (m, 4H); 3.20-3.36 (m, 2H); 3.37 (s, 2H); 3.40-3.60 (m, 2H); 3.80 (s, 3H); 4.28 (s, 1H); 6.70-6.80 (m, 1H); 7.00-7.40 (m, 10H); 7.55 (d, 2H, J=8.4 Hz). Anal. calc. for C34H41N3O2: C, 77.98; H, 7.89; N, 8.02. Found: C, 77.76; H, 7.91; N, 8.12.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 3 days
  3. filtrationAt the end the mixture was filtered under vacuum
  4. customthe liquid phase recovered
  5. customThe solvent was evaporated under vacuum
  6. customthe residual oil purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dc7b9b1b503048ad8d8d245019577365
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609659B2

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