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

HRID 603184Notes

Reaction equation

HRID 603184 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-c7b99397cc64466ea3dce4df42149760
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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