Benzyl Bromide → Ethyl 1-benzylpiperidine-4-carboxylate

HRID 1291185Notes

Reaction equation

HRID 1291185 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 90423Ethyl 1-benzylpiperidine-4-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.62 ml (0.03 mol) of ethyl piperidine-4-carboxylate were dissolved in 50 ml of dimethylformamide and treated with 4.98 ml (0.036 mol) of triethylamine. 3.9 ml (0.033 mol) of benzyl bromide were added while cooling with ice and the mixture was stirred for 10 min., warmed to 40° and stirred under an argon atmosphere for 18 hrs. The solvent was then distilled off, the residue was added to 100 ml of water, extracted three times with 100 ml of ether each time and the organic phase was dried over magnesium sulfate. 5.33 g (72%) of ethyl 1-benzyl-piperidine-4-carboxylate were obtained as a yellow oil. MS: me/e=248 (C15H22NO2+).

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewarmed to 40°
  3. stirringstirred under an argon atmosphere for 18 hrs
  4. distillationThe solvent was then distilled off
  5. additionthe residue was added to 100 ml of water
  6. extractionextracted three times with 100 ml of ether each time
  7. dry with materialthe organic phase was dried over magnesium sulfate

Sources & evidence

ORD record
ord-0176c39f31e344858d6c9dab6251a2ce
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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