Piperidine → Methyl 6-(piperidin-1-ylmethyl)nicotinate

HRID 30452

Reaction equation

HRID 30452 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[N:6][CH:5]=1.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.[OH-].[Na+]>[NH3:6].[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:6][CH:5]=1

Participants

7

Reactant 3

HCID 8082PiperidineHCID 586269Methyl 6-formylpyridine-3-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 222AmmoniaYield 1%HCID 44515770Methyl 6-(piperidin-1-ylmethyl)nicotinateYield 148.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-0f2d767c6c3c4174915665f9ecb1aee8
Source dataset
uspto-grants-2008_09
Patent number
US07423147B2

Linked notes

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