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

HRID 254272노트

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HRID 254272 반응식
[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

참가 물질

5

반응물 1

HCID 586071HCID 586071, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 935Nickel촉매HCID 222Ammonia용매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-864a84661fb7409eb97a854306f15c70
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875617B2

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