Water → 1-[(2-Chloro-4-fluorophenyl)carbonyl]-5-(ethyloxy)-1,2,3,6-tetrahydropyrazine

HRID 1889073Notes

Reaction equation

HRID 1889073 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)=[O:10].F[B-](F)(F)F.[CH2:23]([O+](CC)CC)[CH3:24].O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:12][C:13]([O:17][CH2:23][CH3:24])=[N:14][CH2:15][CH2:16]1)=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2723982Triethyloxonium tetrafluoroborateHCID 25537116HCID 25537116, compound2×

Product 1

HCID 665994581-[(2-Chloro-4-fluorophenyl)carbonyl]-5-(ethyloxy)-1,2,3,6-tetrahydropyrazineYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[(2-Chloro-4-fluorophenyl)carbonyl]-2-piperazinone (0.770 g, 3 mmol, e.g. as prepared in Intermediate 2) was dissolved in Dichloromethane (8 mL) and to this was added triethyloxonium tetrafluoroborate (1.425 g, 7.50 mmol). The reaction mixture was stirred for 18 hours at room temperature. Dichloromethane (30 ml) and iced water (15 ml) were added and the pH was adjusted to pH 7 with solid sodium hydrogen carbonate. The organic phase was separated, washed with brine, dried and evaporated to give crude 1-[(2-chloro-4-fluorophenyl)carbonyl]-5-(ethyloxy)-1,2,3,6-tetrahydropyrazine (0.556 g) which was used without further purification.

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-541fb3c9c9da4c7ea25e1181a041235b
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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