Piperazine → 1-(2,4-Difluorobenzyl)piperazine

HRID 713199Notes

Reaction equation

HRID 713199 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16]>C1COCC1>[F:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[CH2:8][N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 27369481-(Chloromethyl)-2,4-difluorobenzene

Product 1

HCID 27828061-(2,4-Difluorobenzyl)piperazineYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of piperazine (26.5 g, 308 mmol) in THF (350 mL) was heated to 70° C. and 1-(chloromethyl)-2,4-difluorobenzene (5 g, 30.8 mmol) was added. The suspension was heated at 70° C. overnight. The solid (piperazine) was filtered off, and the solvent was removed under reduced pressure. The residue was partitioned between EtOAc and water. The organic layer was dried and concentrated to give the title compound (6 g, 92%). ESI-MS m/z [M+H]+ 213.04.

Workup

  1. temperatureThe suspension was heated at 70° C. overnight
  2. filtrationThe solid (piperazine) was filtered off
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was partitioned between EtOAc and water
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4c0d105bcc774bf7843a0cf0aaa34a63
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

Loading…