Carbon tetrabromide → 3-(Bromomethyl)-1-ethylpiperidine

HRID 2371142Notes

Reaction equation

HRID 2371142 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9]O)[CH2:4]1)[CH3:2].C(Br)(Br)(Br)[Br:12]>O1CCCC1>[Br:12][CH2:9][CH:5]1[CH2:6][CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4]1

Participants

4

Reactant 2

HCID 11205Carbon tetrabromide2×HCID 20439432(1-Ethylpiperidin-3-yl)methanol

Product 1

HCID 215104883-(Bromomethyl)-1-ethylpiperidineYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To mixture of (1-ethylpiperidin-3-yl)methanol (430 mg) and polymer bound triphenylphoshphine (2 g) in tetrahydrofuran (30 mL) was added carbon tetrabromide (1 g). The mixture was stirred for 8 hours before polymer bound triphenylphoshphine (1 g) and carbon tetrabromide (0.5 g) were added. The reaction was stirred overnight at room temperature. The mixture was filtered and evaporated and the residue was purified by silica column chromatography, eluting with a gradient of 0 to 5% 7M NH3/MeOH in dichloromethane to give the title compound as a yellow oil (430 mg, 69%).

Workup

  1. additionwere added
  2. stirringThe reaction was stirred overnight at room temperature
  3. filtrationThe mixture was filtered
  4. customevaporated
  5. customthe residue was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 5% 7M NH3/MeOH in dichloromethane

Sources & evidence

ORD record
ord-6536009f4a9141eb8b5d4131b6853224
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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