Triethylamine → 1-Benzyl 4-ethyl piperidine-1,4-dicarboxylate

HRID 2256033Notes

Reaction equation

HRID 2256033 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.Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>C(Cl)(Cl)Cl>[CH2:23]([O:22][C:20]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1)=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 152896721-Benzyl 4-ethyl piperidine-1,4-dicarboxylateYield 96.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 4-piperidinecarboxylate (14.71 g) and triethylamine (12.04 g) in chloroform (200 mL) was cooled to 0° C. and treated dropwise with benzyl chloroformate (17.91 g). The resulting mixture was stirred at 0° C. for 1 hour, then was warmed to room temperature and was stirred for 12 hours. The mixture was then washed (1N hydrochloric acid, brine), dried, filtered and evaporated to yield a pale yellow oil (26.4 g). The oil was purified by chromatography, with dichloromethane:methanol (95.5) as the eluent, to afford the urethane as a colorless syrup (22.15 g); NMR: 7.35 (m, 5), 5.07 (s, 2), 4.06 (q,2, J=7.0), 3.91 (broad d, 2, J=13.3), 2.95 (broad, 2), 2.53 (m, 1), 1.82 (broad d, 2, J=13.3), 1.41 (m, 2), 1.18 (t, 3, J=7.0).

Workup

  1. temperaturewas warmed to room temperature
  2. stirringwas stirred for 12 hours
  3. washThe mixture was then washed (1N hydrochloric acid, brine)
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d7188aba8e7c496089a47f934fbee6fe
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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