Aluminium lithium hydride → 5-Bromo-2-[(piperidin-1-yl)methyl]pyridine

HRID 2366837Notes

Reaction equation

HRID 2366837 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=O)=[N:12][CH:13]=1>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 26370112(5-Bromopyridin-2-yl)(piperidin-1-yl)methanone

Product 1

HCID 234384095-Bromo-2-[(piperidin-1-yl)methyl]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminium hydride in 1M THF (1.858 mL, 1.858 mmol) was cooled to 0° C. 5-bromo-2-(1-piperidinylcarbonyl)pyridine (for a preparation see Intermediate 25) (250 mg, 0.929 mmol) was dissolved in THF (7 mL) and added dropwise to the LiAlH4 under nitrogen and stirred. After addition to the reductant, the solution was warmed to room temperature. After 1 hour the reactions were filtered, washed with EtOAc (3×10 mL) and evaporated to dryness to give a brown/yellow solid (159 mg). This was purified on a 25+S Biotage silica column, eluting with DCM:2M MeOH/NH3 (1:0 to 97:3). Product-containing fractions were evaporated to dryness to give a dark yellow solid (61 mg).

Workup

  1. additionAfter addition to the reductant
  2. filtrationAfter 1 hour the reactions were filtered
  3. washwashed with EtOAc (3×10 mL)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-2c7a188f54f34ef7bf21db5df7ca42a4
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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