Tetrahydrofuran → N-(2-methylcyclohexyl)-3-methoxy 4-(2-propynyloxy)benzamide

HRID 601980

Reaction equation

HRID 601980 reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]#[CH:20])[C:11](Cl)=[O:12].[CH3:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[NH2:28].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[NH:28][C:11](=[O:12])[C:10]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]#[CH:20])=[C:8]([O:7][CH3:6])[CH:9]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 234322-MethylcyclohexylamineHCID 574456713-Methoxy-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 16058722N-(2-methylcyclohexyl)-3-methoxy 4-(2-propynyloxy)benzamideYield 89.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3 ml of THF and 0.3 g of 3-methoxy-4-(2-propynyloxy)benzoyl chloride were added dropwise 0.19 g of 2-methylcyclohexylamine and 0.16 g of triethylamine in order under ice cooling. The mixture obtained was stirred at room temperature for 4 hours. Then, ethyl acetate was added to the reaction mixture and it was filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.36 g of N-(2-methylcyclohexyl)-3-methoxy 4-(2-propynyloxy)benzamide (hereinafter, described as the compound 2 of the present invention) represented by the formula:

Workup

  1. customThe mixture obtained
  2. filtrationwas filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1281b574172448948b5b01d6ce3af056
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Linked notes

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