Dichloromethane → HCID 86597085, compound

HRID 2220997Notes

Reaction equation

HRID 2220997 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.C(=O)(O)[O-].[Na+].[N:21]#[C:22]Br.[Cl:24]CCl>>[ClH:24].[CH3:15][C@H:10]1[CH2:9][NH:8][CH2:13][C@@H:12]([CH3:14])[N:11]1[C:22]#[N:21]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 10822535tert-butyl (3R,5S)-3,5-dimethylpiperazine-1-carboxylate

Product 1

HCID 86597085HCID 86597085, compound

Procedure

4.00 g of cis-3,5-dimethylpiperazine-1-carboxylic acid tert-butyl ester (prepared according to the method E. Jon Jacobson et. al. J. Med. Chemistry. 1999, Vol. 42, 1123-144) in 91 mL of dichloromethane was treated with sodium bicarbonate (4.7 g) followed by addition of cyanogen bromide (7.5 mL). The reaction mixture was heated at reflux overnight, was filtered, and was purified by column chromatography (0 to 50% ethyl acetate/hexanes) to afford 3.9 g of the title compound as a white solid. 1H NMR (CDCl3, 300 MHz) δ ppm 1.33 (d, 6H, J=6.5 Hz), 1.44 (s, 9H), 2.54 (m, 2H), 3.09 (m, 2H), 4.09 (m, 2H); 13C NMR (CDCl3, 75 MHz) 16.70 (2C), 28.54 (3C), 53.86 (4C), 80.86, 114.10, 154.22.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationwas filtered
  4. customwas purified by column chromatography (0 to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c0c6adf971bb46d69410261576a36856
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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