Ammonia → HCID 18357039, compound

HRID 427432Notes

Reaction equation

HRID 427432 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].N>C(O)C.[Ni]>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 18357053HCID 18357053, compound

Product 1

HCID 18357039HCID 18357039, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(4-cyanophenyl)-4-(4-pyridyl)piperazine (1.8 g) in ethanol saturated with ammonia gas (150 ml) was hydrogenated at 150 atmospheres and 100° C. (using Raney Nickel as catalyst) in a high pressure hydrogenation apparatus for 18 hours. The solution was filtered through diatomaceous earth and the filtrate evaporated to give a solid which was purified by flash chromatography on alumina (ICN Alumina N 32-63) using a mixture of 95:5 dichloromethane:methanol as eluant. The residue was recrystallised from tetrahydrofuran/isohexane to give 1-(4-aminomethylphenyl)-4-(4-pyridyl)piperazine (1.3 g) m.p.168-170° C.; microanalysis, found: C,71.5; H,7.6; N,20.5%; C16H20N4 requires: C,71.6; H,7.5; N,20.9%; NMR: 3.2-3.4(m,4H), 3.4-3.6(m,4H), 3.65(s,2H), 6.8-6.9(d,2H), 6.9-7.0(d,2H), 7.15-7.25(d,2H), 8.15-8.25(d,2H); MS: m/z 269 (MH)+.

Workup

  1. filtrationThe solution was filtered through diatomaceous earth
  2. customthe filtrate evaporated
  3. customto give a solid which
  4. customwas purified by flash chromatography on alumina (ICN Alumina N 32-63)
  5. additiona mixture of 95:5 dichloromethane
  6. customThe residue was recrystallised from tetrahydrofuran/isohexane

Sources & evidence

ORD record
ord-5e36a21b4b384370a344b7ffa1734151
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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