Tetrahydrofuran → N-cyclohexylmethyl-3-fluoro-4-(2-propynyloxy)benzamide

HRID 601986

Reaction equation

HRID 601986 reaction equation
C1COCC1.[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]#[CH:19])[C:10](Cl)=[O:11].[CH:20]1([CH2:26][NH2:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C(OCC)(=O)C>[CH:20]1([CH2:26][NH:27][C:10](=[O:11])[C:9]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]#[CH:19])=[C:7]([F:6])[CH:8]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 76688CyclohexanemethylamineHCID 574456843-Fluoro-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 57445685N-cyclohexylmethyl-3-fluoro-4-(2-propynyloxy)benzamideYield 64.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 10 ml of THF and 0.40 g of 3-fluoro-4-(2-propynyloxy)benzoyl chloride were added 0.45 g of cyclohexylmethylamine and 0.50 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 subjected to silica gel column chromatography to obtain 0.35 g of N-cyclohexylmethyl-3-fluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 22 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

Sources & evidence

ORD record
ord-7518b3286aba4f039c37a31571401569
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Linked notes

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