Tetrahydrofuran → N-(2-methylcyclohexyl)-3,5-dimethoxy-4-(2-propynyloxy)benzamide

HRID 601984

Reaction equation

HRID 601984 reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([O:21][CH3:22])[C:16]=1[O:17][CH2:18][C:19]#[CH:20])[C:11](Cl)=[O:12].[CH3:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[NH2:30].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[NH:30][C:11](=[O:12])[C:10]1[CH:9]=[C:8]([O:7][CH3:6])[C:16]([O:17][CH2:18][C:19]#[CH:20])=[C:15]([O:21][CH3:22])[CH:14]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 234322-MethylcyclohexylamineHCID 574456693,5-Dimethoxy-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 57701169N-(2-methylcyclohexyl)-3,5-dimethoxy-4-(2-propynyloxy)benzamideYield 83.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 15 ml of THF and 0.45 g of 3,5-dimethoxy-4-(2-propynyloxy)benzoyl chloride were added 0.24 g of 2-methylcyclohexylamine and 0.27 g of triethylamine in order at room temperature. The mixture obtained was stirred at room temperature for 4 hours. Then, ethyl acetate was added to the reaction mixture and the mixture was filtered through Celite. The filtrate was concentrated under reduced pressure. The residue obtained was washed with methyl tert-butyl ether and hexane to obtain 0.49 g of N-(2-methylcyclohexyl)-3,5-dimethoxy-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 19 of the present invention) represented by the formula:

Workup

  1. customThe mixture obtained
  2. filtrationthe mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue obtained
  5. washwas washed with methyl tert-butyl ether and hexane

Sources & evidence

ORD record
ord-b9f4cc769b7e4f7ea4346a039bf97167
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Linked notes

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