Cyclohexylamine → Ethyl 3-(cyclohexylamino)propanoate

HRID 1989016Notes

Reaction equation

HRID 1989016 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]([O:10][C:11](=[O:15])[CH2:12][CH2:13]Cl)[CH3:9].C([O-])([O-])=O.[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:8]([O:10][C:11](=[O:15])[CH2:12][CH2:13][NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:9]

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 11430Potassium CarbonateHCID 69341Ethyl 3-chloropropionate

Product 1

HCID 243063Ethyl 3-(cyclohexylamino)propanoateYield 72.3%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Conditions

Temperature
80 °C

Procedure

Cyclohexylamine (0.86 g, 8.7 mmol) and 3-chloro-propionic acid ethyl ester (1.18 g, 8.67 mmol) were combined neat and K2CO3 (1.2 g, 8.7 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 afford 1.25 g (72%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 4.14 (q, 2H, J=7.2 Hz), 2.90 (t, 2H, J=6.6 Hz), 2.50 (t, 2H, J=6.6 Hz), 1.86-1.89 (m, 2H), 1.70-1.75 (m, 2H), 1.58-1.62 (m, 2H), 1.25 (t, 1H, J=7.2 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-85b7e830fa8d43cbb0d0101ee71686d1
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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