Triethylamine → N-(2-methylcyclohexyl)-3-fluoro-4-(2-propynyloxy)benzamide

HRID 601992

Reaction equation

HRID 601992 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]#[CH:14])[C:5](Cl)=[O:6].[CH3:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[NH2:22].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[NH:22][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([O:11][CH2:12][C:13]#[CH:14])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 234322-MethylcyclohexylamineHCID 574456843-Fluoro-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 57445691N-(2-methylcyclohexyl)-3-fluoro-4-(2-propynyloxy)benzamideYield 93.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 5 ml of ethyl acetate and 0.30 g of 3-fluoro-4-(2-propynyloxy)benzoyl chloride were added 0.19 g of 2-methylcyclohexylamine and 0.20 g of triethylamine in order at room temperature. The mixture obtained was stirred at room temperature for 1 hour. 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 was washed in order with methyl tert-butyl ether and hexane to obtain 0.38 g of N-(2-methylcyclohexyl)-3-fluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 34 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. washThe residue was washed in order with methyl tert-butyl ether and hexane

Sources & evidence

ORD record
ord-d708bf979a894f9eb57e9f66ceeec4d0
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Linked notes

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