Cyclopentylamine → Ethyl 3-(cyclopentylamino)propanoate

HRID 1989022Notes

Reaction equation

HRID 1989022 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([O:9][C:10](=[O:14])[CH2:11][CH2:12]Cl)[CH3:8].C([O-])([O-])=O.[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:7]([O:9][C:10](=[O:14])[CH2:11][CH2:12][NH:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:8]

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 11430Potassium CarbonateHCID 69341Ethyl 3-chloropropionate

Product 1

HCID 23053028Ethyl 3-(cyclopentylamino)propanoateYield 83%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Conditions

Temperature
80 °C

Procedure

Cyclopentylamine (1.72 g, 17.5 mmol) and 3-chloro-propionic acid ethyl ester (2.4 g, 18 mmol) were combined neat and K2CO3 (2.4 g, 18 mmol) and a catalytic amount of tetrabutylammonium iodide (ca. 5 mg) was added. The mixture was heated at 80° C. overnight. The resulting mixture was then partitioned between water and DCM. The organic layer was dried (MgSO4) and concentrated to provide 2.68 g (83%) of the title compound. 1H-NMR (400 MHz, CDCl3:) δ ppm 4.13 (p, 2H, J=7.0 Hz), 3.07 (p, 1H, J=6.7 Hz), 2.81-2.94 (m, 4H), 2.51 (t, 1H, J=6.5 Hz), 2.44 (t, 1H, J=7.4 Hz), 1.29-1.88 (m, 6H), 1.25 (t, 3H, J=7.1 Hz)

Workup

  1. customThe resulting mixture was then partitioned between water and DCM
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-51e8acab2f1343aeaff2071a565310f8
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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