Cyclopentanone → HCID 59347775, compound

HRID 20818Notes

Reaction equation

HRID 20818 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][CH:8]1[CH2:12][CH2:11][CH2:10][NH:9]1.[C-:13]#[N:14].[K+]>O>[CH3:7][CH:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:1]1([C:13]#[N:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 9032Potassium CyanideHCID 130032-Methylpyrrolidine

Product 1

HCID 59347775HCID 59347775, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of cyclopentanone (1.34 g, 16 mmol) and 2-methylpyrrolidine (1.36 g; 16 mmol) was cooled to 0° C. (ice bath). A solution of potassium cyanide (1.04 g, 16 mmol) in water (10 ml) was added dropwise over 10 min and the whole mixture stirred vigorously for 18 h at 20° C., and then partitioned between ethyl acetate and water. The organic layer was dried (Na2SO4) and evaporated in vacuo to afford the title compound (2.24 g; 79%). 1NMR (CDCl3) δ: 1.1 (3H, d), 1.45 (1H, m), 1.75-2.05 (9H, m), 2.13 (2H, m), 2.65 (1H, m), 3.1 (2H, m).

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-7dd887b681e1438ebe08219f7499a9ee
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

Loading…