Triethylamine → Benzofuran-2-carboxylic Acid (1-benzo[1,3]dioxol-5-yl-cyclopentylmethyl)-amide

HRID 1818081Notes

Reaction equation

HRID 1818081 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:15][NH2:16])[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1[C:26](Cl)=[O:27].C(N(CC)CC)C>O1CCOCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:15][NH:16][C:26]([C:18]4[O:17][C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=5[CH:19]=4)=[O:27])[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 389492-Benzofurancarbonyl chlorideHCID 199605881-(1,3-Benzodioxol-5-yl)cyclopentanemethanamine

Product 1

HCID 57884168Benzofuran-2-carboxylic Acid (1-benzo[1,3]dioxol-5-yl-cyclopentylmethyl)-amideYield 17.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

C-(1-Benzo[1,3]dioxol-5-yl-cyclopentyl)-methylamine (43.8 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 (83.6 μL, 0.600 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 (13.0 mg, 0.0358 mmol, 17.8%). ESI-MS m/z calc. 363.2, found 364.2 (M+1)+. Retention time of 4.22 minutes.

Workup

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

Sources & evidence

ORD record
ord-f650159990624356842d84c38db064e1
Source dataset
uspto-grants-2009_10
Patent number
US07598412B2

Reaction notes

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