Benzylamine → HCID 18963780, compound

HRID 2226880Notes

Reaction equation

HRID 2226880 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([OH:13])=O)=[C:8]([O:14][CH:15]([CH3:17])[CH3:16])[C:7]=2[CH:18]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([NH:38][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:13])=[C:8]([O:14][CH:15]([CH3:17])[CH3:16])[C:7]=2[CH:18]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 13961721HCID 13961721, compound

Product 1

HCID 18963780HCID 18963780, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-methoxy-3-(1-methylethoxy)-2-benzofurancarboxylic acid (250 mg, 1.00 mmol) [Connor, et al., J. Med. Chem. 35, 935(1992)] and 1,1'-carbonyldiimidazole (211 mg, 1.30 mmol) in 7 mL of tetrahydrofuran is heated at reflux for 1 hour. The reaction solution is cooled to room temperature and benzylamine (0.66 mL, 6.00 mmol) is added and the reaction mixture is stirred at room temperature overnight. The reaction is diluted with ethyl acetate and washed with brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography eluting with ethyl acetate:hexane (1:3 to 1:1) provides 5-methoxy-3-(1-methylethoxy)-N-(phenylmethyl)-2-benzofurancarboxamide in 79% yield; mp=68°-69° C.

Workup

  1. temperatureat reflux for 1 hour
  2. washwashed with brine
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washChromatography eluting with ethyl acetate:hexane (1:3 to 1:1)

Sources & evidence

ORD record
ord-f0a114ff68084a6ebda6643863b15a50
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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