Benzyl chloroformate → Benzyl 4-(2-hydroxyethyl)piperidine-1-carboxylate

HRID 129509Notes

Reaction equation

HRID 129509 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.C(=O)([O-])O.[Na+].[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH2:15]([O:22][C:23]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 739534-PiperidineethanolHCID 516892Sodium Bicarbonate

Product 1

HCID 13971210Benzyl 4-(2-hydroxyethyl)piperidine-1-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 g of 4-piperdine ethanol and 49.2 g of sodium hydrogencarbonate were dissolved in 480 ml of water, in which 55.2 ml of benzyloxycarbonyl chloride was gradually dropped under ice-cooling conditions, followed by agitation for 1 hour as it is. The reaction solution was extracted with chloroform and dried with anhydrous magnesium sulfate. The sulfate was filtered off and the solvent was distilled off, after which the resultant residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:hexane=30:70) to obtain 66.0 g of the captioned compound (yield:65%).

Workup

  1. additionwas gradually dropped under ice-
  2. temperaturecooling conditions
  3. extractionThe reaction solution was extracted with chloroform
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe sulfate was filtered off
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-727d90758f5b439798d9429b7630698f
Source dataset
uspto-grants-1995_11
Patent number
US05468740

Reaction notes

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