Triethylamine → HCID 5322279, compound

HRID 1818075Notes

Reaction equation

HRID 1818075 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:17][NH2:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH:21]=[C:20]1[C:28](Cl)=[O:29].C(N(CC)CC)C>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:17][NH:18][C:28]([C:20]3[O:19][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[CH:21]=3)=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 389492-Benzofurancarbonyl chlorideHCID 75534455092-70-1

Product 1

HCID 5322279HCID 5322279, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

C-[1-(3,4-Dimethoxy-phenyl)-cyclohexyl]-methylamine (276 mg, 1.12 mmol) and Benzofuran-2-carbonyl chloride (223 mg, 1.23 mmol) were dissolved in 6 mL of 1,4-dioxane containing triethylamine (312 μL, 2.24 mmol) at 0° C. The reaction mixture was 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 0-20% ethyl acetate in hexanes. The pure fractions were combined and evaporated to dryness to yield a white solid (195 mg, 0.496 mmol, 44.2%). ESI-MS m/z calc. 393.2, found 394.2 (M+1)+. Retention time of 2.96 minutes. 1H NMR (400 MHz, CD3CN) δ 1.45-2.20 (m, 10H), 3.48 (d, J=6.5 Hz, 2H), 3.80 (s, 3H), 3.83 (s, 3H), 6.68 (s, 1H), 6.92-7.02 (m, 3H), 7.30-7.38 (m, 2H), 7.42-7.49 (m, 1H), 7.51-7.55 (m, 1H), 7.72 (d, J=7.8 Hz, 1H)

Workup

  1. customThe reaction mixture was evaporated 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 0-20% ethyl acetate in hexanes
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-e4b0125852564efc95956c12493ce3d5
Source dataset
uspto-grants-2009_10
Patent number
US07598412B2

Reaction notes

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