Benzylamine → HCID 15296706, compound

HRID 1647861Notes

Reaction equation

HRID 1647861 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:17]([OH:19])=O)=[C:10]2[O:13][CH:14]([CH3:16])[CH3:15])=[CH:5][CH:4]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:17]([NH:39][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:19])=[C:10]2[O:13][CH:14]([CH3:15])[CH3:16])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 14256756HCID 14256756, compound

Product 1

HCID 15296706HCID 15296706, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a room temperature solution of 7-methoxy-1-(1-methylethoxy)-2-naphthalenecarboxylic acid (200 mg, 0.77 mmol) in 5 mL of THF is added N,N-carbonyldiimidazole (162 mg, 1.00 mmol). The solution is heated at reflux for 1 hour and cooled slightly. Benzylamine (0.50 mn) is added and the reaction mixture is stirred at room temperature overnight. The mixture is diluted with ethyl acetate and washed with brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. The crude product is chromatographed on silica gel eluting with hexane:ethyl acetate (2:1) to provide 7-methoxy-1-(1-methylethoxy)-N-(phenylmethyl)-2-naphthalene-carboxamide in 73% yield; mp 88°-90° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled slightly
  4. washwashed with brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is chromatographed on silica gel eluting with hexane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-aa636ee04c5e459b9436e2af3fad0d99
Source dataset
uspto-grants-1995_07
Patent number
US05434188

Reaction notes

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