Triethylamine → HCID 86224995, compound

Participants

Reaction Steps

To a solution of valeryl chloride (342 mg, 338 μl, 2.83 mmol) in dichloromethane (6 ml) and cooled to 0° C. is added a solution of (3-chloro-propyl)-phenethyl-amine (Starting material Q-01e, 560 mg, 2.83 mmol). The colourless solution turns yellow and after 2 min, a solid crystallizes out. Upon dropwise addition of Et3N (315 mg, 409 μl, 2.83 mmol) the solution turns colourless again and the solid dissolves instantaneously. The mixture is allowed to stir for 4 h at which time yet again a solid had crystallized out. Saturated aqueous NH4Cl solution is added and the organic phase is washed once with some saturated aqueous NaHCO3 solution and dried over Na2SO4. The solvent is removed in vacuo and the residue is dried under high vacuum, yielding the title compound as an orange oil: tR=2.48 min (LC-2), ESI-MS (pos.): m/z 282.07 [M+H]+; 1H-NMR (CDCl3): δ (ppm) 0.86-0.97 (m, 3H, CH3), 1.23-1.44 (m, 4H, CH2CH3), 1.55 (quint., 1H, CH2CH2CH3), 1.65 (quint., 1H, CH2CH2CH3), 1.95 (quint., 2H, CH2CH2N), 2.03-2.19 (m, 2H, CH2C═O), 2.90 (t, 2H, CH2Ph), 3.35-3.59 (m, 6H), 7.15-7.34 (m, 2Harom).

Provenance & Evidence