4-BENZHYDRYLPIPERAZIN-1-YL CARBONYL CHLORIDE synthesis
- Product Name:4-BENZHYDRYLPIPERAZIN-1-YL CARBONYL CHLORIDE
- CAS Number:13521-97-6
- Molecular formula:C18H19ClN2O
- Molecular Weight:314.81
Yield:13521-97-6 84%
Reaction Conditions:
with pyridine in dichloromethane at -5 - 20; for 3 h;
Steps:
5.1.1 Benzhydrylpiperazin piperazine-1-carbonyl chloride (2)
A solution containing 1-benzhydrylpiperazine 1 (2.13g, 8.42mmol) and pyridine (1.6mL) in anhydrous CH2Cl2 was added dropwise to the cooled (-5°C) solution of triphosgene (1.00g, 3.37mmol) in anhydrous CH2Cl2. The reaction mixture was slowly warmed up to RT and stirred for 3h. The reaction was quenched by adding CH2Cl2 and water. The organic phase was separated, washed with brine (2×25mL) and dried with anhydrous Na2SO4. The solvent was evaporated and concentrated in vacuo to yield the crude carbonyl chloride as a yellow solid (2.24g, yield 84%) which was used for the next step without further purification. 1H NMR (CDCl3): δ 7.40 (d, 4H), 7.29 (t, 4H, J=7.3Hz), 7.21 (t, 2H, J=7.3Hz), 4.27 (s, 1H), 3.72-3.64 (br s, 4H), 2.44 (s, 4H).
References:
Korhonen, Jani;Kuusisto, Anne;Van Bruchem, John;Patel, Jayendra Z.;Laitinen, Tuomo;Navia-Paldanius, Dina;Laitinen, Jarmo T.;Savinainen, Juha R.;Parkkari, Teija;Nevalainen, Tapio J. [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 23,p. 6694 - 6705]
