Triethylamine → HCID 17901248, compound

HRID 1965965Notes

Reaction equation

HRID 1965965 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].C(N(CC)CC)C.[CH:12]1([C:17](Cl)=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[CH2:1]([NH:4][C:17]([CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:18])[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 239041Propargylamine

Product 1

HCID 17901248HCID 17901248, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve propargylamine (1.5 g, 28.07 mmol) in DCM (50 mL), add triethylamine (7.83 mL, 56.15 mmol) and cool the mixture to 0° C. Add cyclopentanecarbonyl chloride (2.5 g, 18.72 mmol) and warm to room temperature. Stir the reaction mixture for 18 h. Wash the mixture with water (3×50 mL) and hydrochloric acid (2N, 50 mL) and dry the organic phase over MgSO4. Remove the solvent in vacuo and triturate the solid with iso-hexane to give the title compound as a fine white powder (1.51 g, 53%).

Workup

  1. washWash the mixture with water (3×50 mL) and hydrochloric acid (2N, 50 mL)
  2. dry with materialdry the organic phase over MgSO4
  3. customRemove the solvent in vacuo
  4. customtriturate the solid with iso-hexane

Sources & evidence

ORD record
ord-5857607840474a429d32a393c16b922f
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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