Water → HCID 18357043, compound

HRID 427441Notes

Reaction equation

HRID 427441 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.CN(C)CCCN=C=NCC.[N:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1.O>CN(C)C=O>[N:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:31][CH2:32][N:33]([C:4](=[O:6])[C:3]3[CH:7]=[CH:8][C:9]([Br:11])=[CH:10][C:2]=3[F:1])[CH2:34][CH2:35]2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 705171-(4-Pyridyl)piperazineHCID 3026814-Bromo-2-fluorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 18357043HCID 18357043, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-fluoro-4-bromobenzoic acid (0.24 g) in dry dimethylformamide (10 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.17 g) and stirred for 30 minutes at ambient temperature under argon. A solution of 1-(4-pyridyl)piperazine (1.6 g) in dry dimethylformamide (3 ml) was added to the mixture and the mixture cooled to 50° C. The reaction was then allowed to warm to room temperature and stirred overnight. The solution was poured into water and then extracted into diethyl ether, washed with aqueous sodium hydrogen carbonate solution, water, brine. dried (Na2SO4) and evaporated to yield a colourless oil. This oil was then triturated with diethyl ether and recrystallised from ethyl acetate/isohexane to give 1-(4-pyridyl)-4-(2-fluoro-4-bromobenzoyl)piperazine (0.14 g) as a solid, m.p. 125-126° C.: microanalysis, found: C, 52.6; H, 4.1; N, 11.2%; C16H15BrFN3O requires: C, 52.8; H, 4.15; N, 11.5%; NMR: (CDCl3) 3.32(t,2H), 3.46(t,4H), 3.94(t,2H), 6.68(dd,2H), 7.29-7.43(m,3H), 8.33(d,2H); MS: m/z 364 (MH)+.

Workup

  1. temperaturethe mixture cooled to 50° C
  2. temperatureto warm to room temperature
  3. stirringstirred overnight
  4. extractionextracted into diethyl ether
  5. washwashed with aqueous sodium hydrogen carbonate solution, water, brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto yield a colourless oil
  9. customThis oil was then triturated with diethyl ether
  10. customrecrystallised from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-1f5df982d4764ffd9841ce3b0652e2f8
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

Loading…