Piperidine → (4-Isopropyl-piperazin-1-yl)-(6-piperidin-1-ylmethyl-pyridin-3-yl)-methanone

HRID 551576

반응식

HRID 551576 반응식
CO[C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:6][CH:5]=1.COC(=O)[C:21]1C=[CH:25][C:24]([CH:27]=O)=[N:23][CH:22]=1.[NH:30]1CCC[CH2:32][CH2:31]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.[OH-].[Na+]>[NH3:6].[CH:24]([N:23]1[CH2:22][CH2:21][N:30]([C:3]([C:4]2[CH:5]=[N:6][C:7]([CH2:10][N:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)=[CH:8][CH:9]=2)=[O:17])[CH2:31][CH2:32]1)([CH3:25])[CH3:27]

참가 물질

8

반응물 4

HCID 8082PiperidineHCID 586269Methyl 6-formylpyridine-3-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 44515770Methyl 6-(piperidin-1-ylmethyl)nicotinate

생성물 2

HCID 222Ammonia수율 1%HCID 11522780(4-Isopropyl-piperazin-1-yl)-(6-piperidin-1-ylmethyl-pyridin-3-yl)-methanone수율 74%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

실험 절차

6-Piperidin-1-ylmethyl-nicotinic acid methyl ester. To a solution of 6-formyl-nicotinic acid methyl ester (0.200 g, 1.21 mmol) and piperidine (0.14 mL, 1.33 mmol) in DCM (15 mL) was added NaB(OAc)3H (0.380 g, 1.80 mmol). After 18 h, the reaction was diluted with 1 N NaOH (10 mL) and extracted with DCM (2×50 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the residue (SiO2; 1-3% 2 M NH3 in MeOH/DCM) gave the title compound as an oil (0.210 g, 74%).

후처리

  1. extractionextracted with DCM (2×50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2f926d3985e946eeba310fa414bb3afc
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947718B2

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