HCID 69148085, compound → HCID 69145692, compound

HRID 2114813Notes

Reaction equation

HRID 2114813 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[F:23])[CH2:5][N:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][C:7]1=[O:19]>C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[F:23])[CH2:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][C:7]1=[O:19]

Participants

4

Reactant 1

HCID 69148085HCID 69148085, compound

Product 1

HCID 69145692HCID 69145692, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold (0° C.) solution of tert-butyl 4-(3-chloro-4-fluorobenzyl)-3-oxopiperazine-1-carboxylate (3.3 g, 9.63 mmol) in ethyl acetate (150 mL), anhydrous hydrogen chloride gas was bubbled for ten minutes. The resultant solution was stirred at 0° C. for 1 hour, and concentrated under vacuum. The residue was treated with chloroform saturated with ammonia gas. The resultant white suspension was stirred at room temperature for 15 minutes and filtered through a pad of Celite. The filtrate was concentrated under vacuum. The residue was redissolved in benzene, filtered, and concentrated under vacuum to provide the title piperazinone as pale yellow viscous oil.

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe residue was treated with chloroform saturated with ammonia gas
  3. filtrationfiltered through a pad of Celite
  4. concentrationThe filtrate was concentrated under vacuum
  5. dissolutionThe residue was redissolved in benzene
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8b684cfd08e94916bc4c3c00828ca0ff
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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