Benzyl Bromide → 1-Benzylpiperidine

HRID 329656Notes

Reaction equation

HRID 329656 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>CCOCC>[C:2]1([CH2:1][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 8082Piperidine

Product 1

HCID 761901-Benzylpiperidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 11.9 ml of benzyl bromide in 100 ml of ether was added dropwise to a solution of 29.6 ml of piperidine in 100 ml of ether. This mixture was stirred overnight, then filtered. The organic layer was washed with water, then dried and concentrated to an oil. The oil was distilled through a Kugelrohr and the fraction boiling at 75°-85° C., 1.55 mm collected, giving 16.77 g of 1-(phenylmethyl)piperidine as an oil.

Workup

  1. filtrationfiltered
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated to an oil
  5. distillationThe oil was distilled through a Kugelrohr
  6. customthe fraction boiling at 75°-85° C., 1.55 mm collected

Sources & evidence

ORD record
ord-99b2b5e6ae394abdbcb70a51eda9a09e
Source dataset
uspto-grants-1990_01
Patent number
US04892885

Reaction notes

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