Water → HCID 70235886, compound

HRID 427453Notes

Reaction equation

HRID 427453 reaction equation
[H-].[Na+].O[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C([C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1)#N.[OH2:32].[CH3:33][N:34](C)C=O>>[C:33]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[C:6]([O:32][CH2:28][C:27]2[CH:26]=[CH:25][CH:24]=[CH:31][CH:30]=2)[CH:5]=1)#[N:34]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 149869034-(4-(4-Pyridyl)piperazin-1-yl)phenol

Product 1

HCID 70235886HCID 70235886, compound

Procedure

Sodium hydride (120 mg) (50% dispersion in oil) was added to a stirred solution of 1-(4-hydroxyphenyl)-4-(4-pyridyl)piperazine (510 mg) in dimethylformamide (5 ml) under argon. The solution was stirred at ambient temperature for 30 minutes and a solution of 4-cyanobenzylbromide (430 mg) in dimethyl formamide (5 ml) was added dropwise. The solution was stirred at ambient temperature overnight, water (150 ml) added to give a precipitate which was washed with water, dried and recrystallised from ethanol to give 1-(4-cyanobenzyloxyphenyl)-4-(4-pyridyl)piperazine (660 mg), m.p.212-214° C.

Workup

  1. stirringThe solution was stirred at ambient temperature overnight
  2. customto give a precipitate which
  3. washwas washed with water
  4. customdried
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-ee1106556aba498ab772b8b7f32bc91e
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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