Triethylamine → HCID 57884125, compound

HRID 1818079Notes

Reaction equation

HRID 1818079 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:15])([CH3:14])[CH2:12][NH2:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[C:25](Cl)=[O:26].C(N(CC)CC)C>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:15])([CH3:14])[CH2:12][NH:13][C:25]([C:17]2[O:16][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH:18]=2)=[O:26])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 389492-Benzofurancarbonyl chlorideHCID 122597152-(3,4-dimethoxyphenyl)-2-methylpropan-1-amine

Product 1

HCID 57884125HCID 57884125, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(3,4-Dimethoxy-phenyl)-2-methyl-propylamine (106 mg, 0.506 mmol) and benzofuran-2-carbonyl chloride (90.7 mg, 0.502 mmol) were dissolved in 2 mL of 1,4-dioxane containing triethylamine (139 μL, 1.00 mmol). The reaction mixture was stirred for 15 hours, evaporated to dryness, redissolved in dichloromethane, and extracted with 1M hydrochloric acid, 1M sodium hydroxide, and a saturated aqueous solution of sodium chloride. The organic layer dried over sodium sulfate and evaporated to dryness. The crude product was then purified by column chromatography on silica gel using a gradient of 1-30% ethyl acetate in hexanes. The pure fractions were combined and evaporated to dryness to yield a white solid (153 mg, 0.433 mmol, 86.3%). ESI-MS m/z calc. 353.2, found 354.2 (M+1)+. Retention time of 2.99 minutes. 1H NMR (400 MHz, CD3CN) δ 1.38 (s, 6H), 3.60 (s, 2H), 3.81 (s, 3H), 3.83 (s, 3H), 6.85-7.06 (m, 4H), 7.31-7.39 (m, 2H), 7.46 (t, J=8.4 Hz, 1H), 7.52-7.56 (m, 1H), 7.72 (d, J=8.2 Hz, 1H).

Workup

  1. customevaporated to dryness
  2. dissolutionredissolved in dichloromethane
  3. extractionextracted with 1M hydrochloric acid, 1M sodium hydroxide
  4. dry with materialThe organic layer dried over sodium sulfate
  5. customevaporated to dryness
  6. customThe crude product was then purified by column chromatography on silica gel using a gradient of 1-30% ethyl acetate in hexanes
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-0cbb3fce00a64ac88811a7745d9b0492
Source dataset
uspto-grants-2009_10
Patent number
US07598412B2

Reaction notes

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