Piperazine → HCID 18186789, compound

HRID 1357595Notes

Reaction equation

HRID 1357595 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+].N[C@H](C(O)=O)[C@@H](C)O>C(#N)C.ClCCl>[CH2:8]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[N:3]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 4837PiperazineHCID 6288L-ThreonineHCID 11430Potassium CarbonateHCID 18186874HCID 18186874, compound

Product 1

HCID 18186789HCID 18186789, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of the product from step 1 above (0.83 g, 4.0 mmol), piperazine (1.1 g, 12.8 mmol) and K2CO3 (0.62 g, 4.49 mmol) in acetonitrile (7 mL) was stirred at 85° C. for 8.5 h. Thr reaction mixture was diluted with dichloromethane, filtered and concentrated in vacuo. The semi-solid residue was purified by silica gel chromatography (20×4 cm) using CHCl3/MeOH (9:1) as eluent. The resulting oil was redissolved in CHCl3 and filtered through a short (4 cm) plug of alumina using ether/MeOH (96:4) as eluent. Solvent removal in vacuo furnished 0.59 g (57%) of the title compound as an oil which became semi-solid upon refrigeration. HRMS m/z calcd for C15H18N4 (M)+ 254.1531, found 254.1527. Anal. (C15H18N4) C, H, N.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe semi-solid residue was purified by silica gel chromatography (20×4 cm)
  4. dissolutionThe resulting oil was redissolved in CHCl3
  5. filtrationfiltered through a short (4 cm) plug of alumina
  6. customSolvent removal in vacuo

Sources & evidence

ORD record
ord-16e3b3eea9af4dd098653ba7f2c06d67
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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