Triethylamine → HCID 57884154, compound

HRID 1818080Notes

Reaction equation

HRID 1818080 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2([CH2:18][NH2:19])[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[O:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH:22]=[C:21]1[C:29](Cl)=[O:30].C(N(CC)CC)C>O1CCOCC1>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]2([CH2:18][NH:19][C:29]([C:21]3[O:20][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[CH:22]=3)=[O:30])[CH2:14][CH2:15][CH2:16][CH2:17]2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 389492-Benzofurancarbonyl chlorideHCID 66724548HCID 66724548, compound

Product 1

HCID 57884154HCID 57884154, compoundYield 11.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

C-[1-(3,4,5-Trimethoxy-phenyl)-cyclopentyl]-methylamine (53.1 mg, 0.200 mmol) and benzofuran-2-carbonyl chloride (36.1 mg, 0.200 mmol) were dissolved in 2 mL of 1,4-dioxane containing triethylamine (84 μL, 0.60 mmol). The reaction mixture was stirred for 15 hours, evaporated to dryness, and purified by reverse phase preparative liquid chromatography to yield the pure product (9.59 mg, 0.0234 mmol, 11.7%). ESI-MS m/z calc. 409.2, found 410.4 (M+1)+. Retention time of 3.29 minutes.

Workup

  1. customevaporated to dryness
  2. custompurified by reverse phase preparative liquid chromatography

Sources & evidence

ORD record
ord-4e48b9bde2f44b27a07999bcd6a429dd
Source dataset
uspto-grants-2009_10
Patent number
US07598412B2

Reaction notes

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