Piperidine → 3-Bromo-5-(piperidin-1-ylmethyl)pyridine

HRID 30470

반응식

HRID 30470 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:3]=1

참가 물질

5

반응물 3

HCID 8082PiperidineHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 671888053-Bromo-5-(piperidin-1-ylmethyl)pyridine수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-Bromo-pyridine-3-carbaldehyde (0.190g, 1 mmol), NaB(OAc)3H (0.320 g, 1.50 mmol) and piperidine (0.090 g, 1.05 mmol) were suspended in DCM (8 mL) and the reaction mixture was stirred overnight at rt. The reaction was quenched by the addition of 1 M NaOH solution (5 mL) and the mixture was stirred for 1 h. The reaction mixture was extracted with DCM (3×15 mL). The organic extracts were combined, dried over Na2SO4, filtered, and concentrated to yield a crude oily product (0.18 g, 71%). This crude product was carried to the next step.

후처리

  1. customThe reaction was quenched by the addition of 1 M NaOH solution (5 mL)
  2. stirringthe mixture was stirred for 1 h
  3. extractionThe reaction mixture was extracted with DCM (3×15 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f27ee76980884117baec2023d5ba8948
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423147B2

연결된 노트

불러오는 중…