Sodium Carbonate → Ethyl 3-(hydroxymethyl)piperidine-1-carboxylate

HRID 1274113Notes

Reaction equation

HRID 1274113 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.C([O-])([O-])=O.[Na+].[Na+].Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(Cl)(Cl)Cl.O>[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:4]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 19261731Ethyl 3-(hydroxymethyl)piperidine-1-carboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 3-hydroxymethyl-piperidine (0.6 mol) and Na2CO3 (130 g) in CHCl3 (600 ml) and water (600 ml) was stirred at 10° C. Ethyl chloroformate (115 g) was added dropwise (temperature was kept at 10° C.). The mixture was stirred until the temperature reached room temperature and the reaction mixture was stirred overnight. Water (500 ml) was added. The organic layer was separated, washed with water, dried, filtered and the solvent was evaporated, yielding 110 g (98%) of (±)-ethyl 3-(hydroxymethyl)-1-piperidinecarboxylate (interm. 17).

Workup

  1. stirringThe mixture was stirred until the temperature
  2. customreached room temperature
  3. stirringthe reaction mixture was stirred overnight
  4. customThe organic layer was separated
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-204971d77c894ca6a2471580a7dfba68
Source dataset
uspto-grants-2000_12
Patent number
US06156757

Reaction notes

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