Water → HCID 18357115, compound

HRID 427437Notes

Reaction equation

HRID 427437 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[H-].[Na+].[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.O>CN(C)C=O>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:20][C:19]3[CH:22]=[CH:23][C:16]([Br:15])=[CH:17][CH:18]=3)[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 705171-(4-Pyridyl)piperazine

Product 1

HCID 18357115HCID 18357115, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-pyridyl)piperazine (0.33 g) in dry dimethylformamide (15 ml) was treated with sodium hydride (0.14 g) (45-55% dispersion in oil). The reaction mixture was then stirred for 45 minutes at ambient temperature under argon. 4-Bromobenzyl bromide (0.58 g) was added and the mixture heated slowly to 60° C. and then maintained at this temperature for 2 hours. The resulting mixture was then poured into water, basified with aq.NaHCO3 solution and then extracted with diethyl ether. The organic extracts were then washed with aq.NaHCO3, water, brine, dried (Na2SO4) and evaporated. The residue was recrystallised from acetonitrile to give 1-(4-pyridyl)-4-(4-bromobenzyl)piperazine (0.2 g) as a solid, m.p. 140-141° C.; microanalysis, found: C,55.3; H,5.2; N,12.0%; C16H18N3Br requires: C,55.4; H,5.7; N,12.1%; NMR: (CDCl3) 2.54(t,4H); 3.2(t,4H); 3.51(s,2H); 6.66(d,2H); 7.23(d,2H); 7.46(d,2H); 8.29(d,2H); MS: m/z 332 (MH)+.

Workup

  1. temperaturethe mixture heated slowly to 60° C.
  2. temperaturemaintained at this temperature for 2 hours
  3. extractionNaHCO3 solution and then extracted with diethyl ether
  4. washThe organic extracts were then washed with aq
  5. dry with materialNaHCO3, water, brine, dried (Na2SO4)
  6. customevaporated
  7. customThe residue was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-ce13ed36ea2f4faeae2a8a7eba8699ac
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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