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

HRID 30470

Reaction equation

HRID 30470 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f27ee76980884117baec2023d5ba8948
Source dataset
uspto-grants-2008_09
Patent number
US07423147B2

Linked notes

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