Pyridine → HCID 86585989, compound

HRID 1794053Notes

Reaction equation

HRID 1794053 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10](CC)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1[CH:21]=[CH:20]C=CC=1.[Cl:22][C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:23]([Cl:22])=[O:25])[CH2:12][CH:13]1[CH2:20][CH3:21])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 22219867tert-Butyl 3-ethylpiperazine-1-carboxylate

Product 1

HCID 86585989HCID 86585989, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

a solution of (RS) 4-tert-butoxycarbonyl-2-ethylpiperazine (3.95 g) and pyridine (1.64 ml) in DCM (35 ml) was added dropwise to a stirred solution of triphosgene (2.1 g) in DCM (100 ml) at 0° C. under Ar. The mixture was warmed to room temperature, stirred for 30 min then washed with water (100 ml) and brine (100 ml). The organic solution was dried (sodium sulfate) and concentrated in vacuo. The residue was dissolved in isohexane, filtered and concentrated in vacuo to give the product as a clear oil (3.73 g) which was used without further purification; δH (400 MHz, CDCl3) 4.39–3.80 (4H, m), 3.39–2.69 (3H, m), 1.66 (2H, m), 1.47 (9H, s), 0.96 (2.7H, d, J 7 Hz) and 0.89 (0.3H, d, J 7 Hz); GC (150° C.-10 min-320° C.) 83%, 8.72 min.

Workup

  1. washthen washed with water (100 ml) and brine (100 ml)
  2. dry with materialThe organic solution was dried (sodium sulfate)
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in isohexane
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69a05dc53db84acea7bde16f656daa85
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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