Water → HCID 18357094, compound

HRID 427438Notes

Reaction equation

HRID 427438 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+].[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1)#[N:16].O>CN(C)C=O>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:21][C:20]3[CH:23]=[CH:24][C:17]([C:15]#[N:16])=[CH:18][CH:19]=3)[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 705171-(4-Pyridyl)piperazineHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 18357094HCID 18357094, compoundYield 14.2%

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 30 minutes at ambient temperature under argon. 4-Cyanobenzyl bromide (0.41 g) was added and the mixture heated slowly to 80° 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 (MgSO4) and evaporated. The residue was recrystallised from toluene/hexane to give 1-(4-pyridyl)-4-(4-cyanobenzyl)piperazine (0.08 g) as a solid. m.p. 137-138° C.; microanalysis, found: C, 73.3; H, 6.5; N, 19.8%; C17H18N4 requires: C, 73.4; H, 6.5; N, 20.1%; NMR: (CDCl3) 2.56(t,4H); 3.35(t,4H); 3.61(s,2H); 6.67(dd,2H); 7.49(d,2H); 7.63(d,2H); 8.28(dd,2H); MS: m/z 279(MH)+.

Workup

  1. temperaturethe mixture heated slowly to 80° 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 materialbrine, dried (MgSO4)
  6. customevaporated
  7. customThe residue was recrystallised from toluene/hexane

Sources & evidence

ORD record
ord-6d044c5f3a904af78126e64d1d6aa04d
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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