Triethylamine → 1-(p-Nitrobenzyloxycarbonyl)-4-hydroxypiperidine

HRID 891711Notes

Reaction equation

HRID 891711 reaction equation
Cl.[OH:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[N+:9]([C:12]1[CH:22]=[CH:21][C:15]([CH2:16][O:17][C:18](Cl)=[O:19])=[CH:14][CH:13]=1)([O-:11])=[O:10].C(N(CC)CC)C>C(Cl)Cl.N1C=CC=CC=1>[OH:2][CH:3]1[CH2:8][CH2:7][N:6]([C:18]([O:17][CH2:16][C:15]2[CH:14]=[CH:13][C:12]([N+:9]([O-:11])=[O:10])=[CH:22][CH:21]=2)=[O:19])[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 782054-Nitrobenzyl chloroformateHCID 162124994-Hydroxypiperidinium chloride

Product 1

HCID 132927091-(p-Nitrobenzyloxycarbonyl)-4-hydroxypiperidineYield 48.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxypiperidine hydrochloride (3.0 g, 21.8 mmol) in a mixture of methylene chloride (90 ml) and pyridine (15 ml) were added chloroformic acid p-nitrobenzyl ester (15.4 g, 72.0 mmol) and triethylamine (13.1 ml, 93.8 mmol) in an ice bath. The mixture was stirred at room temperature for 3 days. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The obtained organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:1)→ethyl acetate as the eluant to afford 4-hydroxy-1-(p-nitrobenzyloxycarbonyl)piperidine (2.96 g, yield 48%) as pale yellow crystals.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe obtained organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-72b852c969de479d94b76999968f1257
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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