Potassium Iodide → 1-[4,4-Bis(4-fluorophenyl)butyl]homopiperazine

HRID 2073490Notes

Reaction equation

HRID 2073490 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:16][CH2:17][CH2:18]Br)=[CH:11][CH:10]=1.[I-].[K+]>CN(C)C=O.C(Cl)Cl>[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[CH2:16][CH2:17][CH2:18][N:1]2[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 68163Hexahydro-1,4-diazepineHCID 937631,1'-(4-Bromobutylidene)bis[4-fluorobenzene]

Product 1

HCID 198571681-[4,4-Bis(4-fluorophenyl)butyl]homopiperazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

24 g (0.24 mol) of 1,4-diazacycloheptane, 7.8 g (0.024 mol) of 4,4-bis(4-fluorophenyl)butyl bromide and 0.14 g of potassium iodide were stirred in 60 ml of dimethylformamide at room temperature for 4 hours. The solvent was stripped off in vacuo, the residue was taken up in methylene chloride, the mixture was extracted by shaking with 2N HCl, the acid phase was brought to pH 11 with concentrated NaOH and extracted with methylene chloride and the extracts were dried and concentrated.

Workup

  1. extractionthe mixture was extracted
  2. extractionextracted with methylene chloride
  3. customthe extracts were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-085e3376fa71417bba37c2ac20552cc8
Source dataset
uspto-grants-1990_04
Patent number
US04918073

Reaction notes

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