Potassium Carbonate → HCID 28351514, compound

HRID 1696698Notes

Reaction equation

HRID 1696698 reaction equation
C(O)(=O)[C@H:2]([C:4]1C=CC=C[CH:5]=1)[OH:3].[CH3:12][C@H:13]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]1.BrCCCO.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:12][C@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([CH2:5][CH2:4][CH2:2][OH:3])[CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 66784333HCID 66784333, compound

Product 1

HCID 28351514HCID 28351514, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3S)-3-methylpiperidin(S)-(+)-mandelate (19.9 g, 79.1 mmol), 3-bromo-1-propanol (10 g, 71.9 mmol) and potassium carbonate (14.9 g, 108 mmol) were mixed in THF (200 mL), and heated under reflux for 30 hours. The insoluble matter was separated by filtration, the filtrate was concentrated, and ethyl acetate and hexane were added to the residue. The resulting insoluble matter was separated by filtration, the filtrate was concentrated and evaporated under reduced pressure to obtain the intended product (9.6 g, 85%) as a colorless oil. (3S)-3-methylpiperidin (S)-(+)-mandelate was synthesized according to the method described in a reference (J. Org. Chem., 1987, Vol. 52, p. 5466).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 hours
  3. customThe insoluble matter was separated by filtration
  4. concentrationthe filtrate was concentrated
  5. additionethyl acetate and hexane were added to the residue
  6. customThe resulting insoluble matter was separated by filtration
  7. concentrationthe filtrate was concentrated
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-90cabc65c44a4ea3ae9a7a9015cf84be
Source dataset
uspto-grants-2012_04
Patent number
US08163770B2

Reaction notes

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