Trifluoroacetic acid → HCID 63040760, compound

Participants

Reaction Steps

A solution of 1-[3,3-bis(ethyloxy)propyl]-2-piperidinone (1.52 g, 6.61 mmol) in CH2Cl2 (100 mL) under nitrogen was treated with trifluoroacetic acid (TFA) (1.5 mL, 19.5 mmol) and stirred at ambient temperature for 1 h. After adding an additional 1.5 mL of TFA and monitoring by TLC (EtOAc, KMnO4 stain) for complete consumption of starting materials the reaction mixture was partitioned between CH2Cl2 and 1:1 Sat. NaHCO3:water (150 mL) solution. Extracted the aqueous with CH2Cl2 two additional times before combining the organics, washing them with brine, drying over MgSO4, filtering, and concentrating in vacuo to provide the desired product as a clear oil: 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.78-1.91 (m, 4 H), 2.67 (t, J=6.11 Hz, 2 H), 2.85 (td, J=6.42, 0.91 Hz, 2 H), 3.50 (t, J=5.48 Hz, 2 H), 3.71 (t, J=6.32 Hz, 2 H), 9.53-9.58 (m, 1 H); ES+ MS: 156 (M+H+).

Provenance & Evidence