Triethylamine → 1-ethyl-1-methylpropyl 2-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]-2-oxoethylcarbamate

HRID 2236012Notes

Reaction equation

HRID 2236012 reaction equation
[CH2:1]([C:3]([CH3:14])([O:6][C:7]([NH:9][CH2:10][C:11]([OH:13])=O)=[O:8])[CH2:4][CH3:5])[CH3:2].[CH:15]1[C:25]2[CH:24]=[CH:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[C:20](=[C:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl.CN(C)C=O>[CH:15]1[C:25]2[CH:24]=[CH:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[C:20](=[C:30]3[CH2:31][CH2:32][N:33]([C:11](=[O:13])[CH2:10][NH:9][C:7](=[O:8])[O:6][C:3]([CH2:1][CH3:2])([CH3:14])[CH2:4][CH3:5])[CH2:34][CH2:35]3)[C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 1597184-(5H-Dibenzo(a,d)cyclohepten-5-ylidene)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 85792234{[(1-Ethyl-1-methylpropoxy)carbonyl]amino}acetic acid

Product 1

HCID 598539191-ethyl-1-methylpropyl 2-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]-2-oxoethylcarbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

284 mg (1.40 mmol) of {[(1-ethyl-1-methylpropoxy)carbonyl]amino}acetic acid, 320 mg (1.17 mmol) of 4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-piperidine and 322 mg (1.68 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride were dissolved in a mixed solvent of 15 ml of dichloromethane and 5 ml of dimethylformamide. 0.23 ml (1.68 mmol) of triethylamine and 14.7 mg (0.12 mmol) of dimethylaminopyridine were added to the obtained solution, and they were stirred at room temperature overnight. After the concentration under reduced pressure, ethyl acetate was added to the reaction mixture. The resultant mixture was washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was purified by the silica gel chromatography (hexane: dichloromethane=95:5 to 2:3) to obtain the title compound.

Workup

  1. concentrationAfter the concentration under reduced pressure, ethyl acetate
  2. additionwas added to the reaction mixture
  3. washThe resultant mixture was washed with saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by the silica gel chromatography (hexane: dichloromethane=95:5 to 2:3)

Sources & evidence

ORD record
ord-a750d5dd7c22433eb98076758396b27d
Source dataset
uspto-grants-2010_05
Patent number
US07713957B2

Reaction notes

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