Chloroform → HCID 68592779, compound

HRID 2220999Notes

Reaction equation

HRID 2220999 reaction equation
C(OC([N:8]1[CH2:13][C@H:12]([CH3:14])[NH:11][C@H:10]([CH3:15])[CH2:9]1)=O)(C)(C)C.CC(C=C)=[O:18].C(Cl)(Cl)[Cl:22]>>[ClH:22].[CH3:14][C@H:12]1[CH2:13][NH:8][CH2:9][C@@H:10]([CH3:15])[N:11]1[OH:18]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 6570Methyl vinyl ketoneHCID 10822535tert-butyl (3R,5S)-3,5-dimethylpiperazine-1-carboxylate

Product 1

HCID 68592779HCID 68592779, compound

Procedure

Cis-3,5-dimethylpiperazine-1-carboxylic acid tert-butyl ester (3.00 g; prepared according to the method E. Jon Jacobson et. al.: J. Med. Chemistry. 1999, Vol. 42, 1123-144) in 47 mL chloroform was treated with methylvinylketone (1.7 mL) at room temperature and heated at reflux for two days. The reaction was then concentrated, diluted with THF and heated at reflux for 1 day before purifying by column chromatography (0 to 10% MeOH/DCM) to afford 0.865 g of the title compound as a clear, colorless oil. 1H NMR (CDCl3, 300 MHz) δ ppm 1.08 (d, 2H, J=6.07 Hz), 1.47 (s, 9H), 2.17 (s, 3H), 2.52 (m, 6H), 3.10 (m, 2H), 2.86 (bs, 2H); 13C NMR (CDCl3, 75 MHz) 17.6 (2C), 28.62 (5C), 30.8, 37.34, 42.46, 53.57 (4C), 79.85, 154.49, 208.29.

Workup

  1. customprepared
  2. temperatureheated
  3. temperatureat reflux for two days
  4. concentrationThe reaction was then concentrated
  5. additiondiluted with THF
  6. temperatureheated
  7. temperatureat reflux for 1 day
  8. custombefore purifying by column chromatography (0 to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-2b1da88eeecc4fa19f90836e5fe67de1
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

Loading…