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

HRID 1912342Notes

Reaction equation

HRID 1912342 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dc7b9b1b503048ad8d8d245019577365
Source dataset
uspto-grants-2013_12
Patent number
US08609659B2

Reaction notes

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