Piperazine → HCID 23044998, compound

HRID 2107949Notes

Reaction equation

HRID 2107949 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[Cl:25][C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1.N1CCNCC1.CCOC(C)=O>CN(C=O)C.CCOCC.CCO>[ClH:25].[F:24][C:21]1[CH:20]=[CH:19][C:18]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][N:15]([C:26]3[N:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH2:16][CH2:17]2)=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 4837PiperazineHCID 8857Ethyl AcetateHCID 744042-ChloropyrimidineHCID 797291-(4,4-Bis(4-fluorophenyl)butyl)piperazine

Product 1

HCID 23044998HCID 23044998, compoundYield 65.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

8.3 g (0.025 mole) of 1-[4,4-bis(p-fluorophenyl)butyl]-piperazine and 3.1 g (0.027 mole) of 2-chloropyrimidin were heated in 5 ml DMF at 150° C. until TLC showed the disappearance of the starting piperazine derivative. After cooling EtOAc (50 ml) and EtOH (enough to get a clear solution) were added. Ether was added, whereby the desired product crystallized. Recrystallization from EtOH, EtOAc+ether yielded 7.3 g (65%) of the title compound (2:1), m.p. 195°-97° C.

Workup

  1. customto get a clear solution)
  2. additionwere added
  3. customwhereby the desired product crystallized
  4. customRecrystallization from EtOH, EtOAc+ether

Sources & evidence

ORD record
ord-6ffeffc372844803904d8950ef8d6f88
Source dataset
uspto-grants-1990_06
Patent number
US04937245

Reaction notes

Loading…