Triphosgene → Hexahydropyrazino[1,2-c][1,3]oxazin-6(2H)-one

HRID 590557Notes

Reaction equation

HRID 590557 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10](CCO)[CH2:9]1)=[O:7])([CH3:4])(C)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>ClCCl.CCN(C(C)C)C(C)C>[CH2:10]1[CH:9]2[N:8]([C:6](=[O:7])[O:5][CH2:1][CH2:4]2)[CH2:13][CH2:12][NH:11]1

Participants

5

Reactant 2

HCID 94429TriphosgeneHCID 53407692tert-Butyl 3-(2-hydroxyethyl)piperazine-1-carboxylate

Product 1

HCID 71757625Hexahydropyrazino[1,2-c][1,3]oxazin-6(2H)-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

3-(2-Hydroxy-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (58 mg, 0.25 mmol) was dissolved in 4 mL of dichloromethane and 1 mL of DIPEA, and then triphosgene (27 mg, 0.09 mmol) was added at room temperature. The reaction mixture was stirred for 30 minutes, and the solvent was removed in vacuo. The residue was dissolved in 3 mL of dichloromethane and 1 mL of TFA. After the reaction mixture was stirred for 1 hour, the solvent was removed in vacuo to give hexahydro-pyrazino[1,2-c][1,3]oxazin-6-one trifluoro acetitic acid salt (Compound D) as a crude product which was used directly without further purification. LC/MS: calc'd 157 (MH+), exp 157 (MH+).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in 3 mL of dichloromethane
  3. stirringAfter the reaction mixture was stirred for 1 hour
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6abc9841941348a98afd34b0db7fc32a
Source dataset
uspto-grants-2016_01
Patent number
US09233978B2

Reaction notes

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