Sodium hydride → 4-(4-Bromophenylmethyl)-1-(1-(4-pyridyl)piperidin-4-ylcarbonyl)piperazine

HRID 2288734Notes

Reaction equation

HRID 2288734 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[O:14])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[H-].[Na+].[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>CN(C)C=O>[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N:18]2[CH2:17][CH2:16][N:15]([C:13]([CH:10]3[CH2:11][CH2:12][N:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)[CH2:8][CH2:9]3)=[O:14])[CH2:20][CH2:19]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 108022941-(4-Pyridylpiperidin-4-ylcarbonyl)piperazine

Product 1

HCID 107180884-(4-Bromophenylmethyl)-1-(1-(4-pyridyl)piperidin-4-ylcarbonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(1-(4-Pyridyl)piperidin-4ylcarbonyl)piperazine (0.722 g) was dissolved in dry dimethylformamide (22 mL) and treated with sodium hydride (0.19 g, 45-55% dispersion, 4 mmol) under argon atmosphere. The resultant mixture was then allowed to stir for 30 minutes before the addition of 4-bromobenzyl bromide (0.66 g). The reaction was then stirred at room temperature for 2 hours and then quenched by pouring into water, basifying with saturated aq.NaHCO3 and then extracting with diethyl ether. The combined organic extracts were then washed with water, brine, dried (MgSO4) and then evaporated to afford a crude, cream solid which was then recrystallised twice from ethyl acetate/isohexane to give 4-(4-bromophenylmethyl)-1-(1-(4-pyridyl)piperidin-4-ylcarbonyl)piperazine as a white solid; m.p. 148-149° C.;

Workup

  1. customquenched
  2. additionby pouring into water
  3. extractionNaHCO3 and then extracting with diethyl ether
  4. washThe combined organic extracts were then washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto afford a crude, cream solid which
  8. customwas then recrystallised twice from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-9770a8400cad4d6f869edc3f09a22832
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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