HCID 586071, compound → 1-(4-Aminobutyl)-4-(2-methoxyphenyl)piperazine

HRID 254272Notes

Reaction equation

HRID 254272 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH2:8][CH2:7]1)#[N:2]>CO.N.[Ni]>[NH2:2][CH2:1][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH2:8][CH2:7]1

Participants

5

Reactant 1

HCID 586071HCID 586071, compound

Product 1

HCID 109999031-(4-Aminobutyl)-4-(2-methoxyphenyl)piperazineYield 88.6%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

1-N(3-cyanopropyl)-4-N(2-methoxyphenyl)piperazine (5 g) was dissolved in a mixture of MeOH and aqueous ammonia (28%) in 1/1 ratio (20 mL) and the mixture is shook in a Parr apparatus in presence of Raney/Ni (500 mg) at 60 psi for 18 h. The catalyst is removed by filtration and the filtrate concentrated in vacuo. The residue is taken in AcOEt, the organic layer is washed three times with H2O, dried over Na2SO4 and concentrated. The oily residue is dissolved in EtOH and aqueous HCl (37%, 15 mL) is added. The obtained hydrochloride salt is crystallized in Et2O to give the title compound B2 (4.5 g, 81%) as crystals. 1H NMR (200 MHz, CDCl3) δ 1.48-1.64 (m, 4H), 2.16 (s, 2H), 2.36-2.43 (m, 2H), 2.57-2.62 (m, 4H), 2.69-2.76 (m, 2H), 3.18-3.23 (m, 4H), 3.79 (s, 3H), 6.40-6.56 (m, 3H), 7.20 (t, 1H). 13C NMR (50 MHz, CDCl3) δ 24.2, 31.6, 42.0, 49.0, 53.1, 55.1, 58.4, 102.4, 104.3, 108.8, 129.7, 152.6, 160.5.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. washthe organic layer is washed three times with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. dissolutionThe oily residue is dissolved in EtOH
  7. additionaqueous HCl (37%, 15 mL) is added
  8. customThe obtained hydrochloride salt is crystallized in Et2O

Sources & evidence

ORD record
ord-864a84661fb7409eb97a854306f15c70
Source dataset
uspto-grants-2011_01
Patent number
US07875617B2

Reaction notes

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