Piperidine → (4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethyl-pyridin-2-yl)-methanone

HRID 551580노트

반응식

HRID 551580 반응식
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:14][N:13]=2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C(N1CCN(C(C2N=CC(C=O)=CC=2)=O)CC1)(C)C.N1CCCCC1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C(Cl)Cl>[NH3:4].[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)=[CH:14][N:13]=2)=[O:11])[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

참가 물질

8

반응물 5

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 25126154(4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethyl-pyridin-2-yl)-methanoneHCID 445157766-(4-Isopropyl-piperazine-1-carbonyl)-pyridine-3-carbaldehyde

생성물 2

HCID 222Ammonia수율 4%HCID 25126154(4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethyl-pyridin-2-yl)-methanone수율 9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethyl-pyridin-2-yl)-methanone. To a solution of 6-(4-isopropyl-piperazine-1-carbonyl)-pyridine-3-carbaldehyde (0.250 g, 0.96 mmol) and piperidine (0.11 mL, 1.10 mmol) in DCM (20 mL) was added NaB(OAc)3H (0.300 g, 1.44 mmol). After 18 h, 1 N NaOH (15 mL) was added and the mixture was extracted with DCM (3×25 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the resulting residue (SiO2: 4-8% 2 M NH3 in MeOH/DCM) gave the title compound as an oil (0.030 g, 9%). MS (ESI): exact mass calcd. for C19H30N4O, 330.2; m/z found, 331.5 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.49 (s, 1H), 7.77 (dd, J=7.8, 2.0, 1H), 7.58 (d, J=7.8, 1H), 3.82 (t, J=5.0, 2H), 3.61 (t, J=5.0, 2H), 3.49 (s, 2H), 2.75-2.72 (m, 1H), 2.62 (t, J=5.0, 2H), 2.51 (t, J=5.0, 2H), 2.37 (br s, 4H), 1.60-1.54 (m, 4H), 1.45-1.43 (m, 2H), 1.05 (d, J=6.6, 6H).

후처리

  1. extractionthe mixture was extracted with DCM (3×25 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e9c9123234954fbeb2af1b7d6773f766
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947718B2

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