Triethylamine → 1-(3-Cyano-5-fluorophenyl)-4-(2,2,2-trichloroethoxycarbonyl)piperazine

HRID 564870Notes

Reaction equation

HRID 564870 reaction equation
Cl.[C:2]([C:4]1[CH:5]=[C:6]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:7]=[C:8]([F:10])[CH:9]=1)#[N:3].C(N(CC)CC)C.Cl[C:25]([O:27][CH2:28][C:29]([Cl:32])([Cl:31])[Cl:30])=[O:26]>ClCCl>[C:2]([C:4]1[CH:5]=[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:25]([O:27][CH2:28][C:29]([Cl:32])([Cl:31])[Cl:30])=[O:26])[CH2:13][CH2:12]2)[CH:7]=[C:8]([F:10])[CH:9]=1)#[N:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 18545236HCID 18545236, compound

Product 1

HCID 185454131-(3-Cyano-5-fluorophenyl)-4-(2,2,2-trichloroethoxycarbonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In 30 ml of dichloromethane was suspended 2.54 g of 1-(3-cyano-5-fluorophenyl)piperazine hydrochloride, and the suspension was cooled to 0° C. To the suspension were added 7.3 ml of triethylamine and 3 ml of 2,2,2-trichloroethyl chloroformate, followed by stirring at room temperature for 2 hours. The reaction mixture was washed with water and then with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was subjected to silica gel column chromatography using chloroform as a developing solvent. The fraction containing the desired compound was concentrated to give 4.79 g of the title compound.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialwith a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated
  4. additionThe fraction containing the desired compound
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-e5095b7dc2d94991b3062272bac7517e
Source dataset
uspto-grants-2001_01
Patent number
US06169086A

Reaction notes

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