Potassium Carbonate → HCID 28351514, compound

HRID 2111848Notes

Reaction equation

HRID 2111848 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.C([O-])(=O)[C@H:9]([C:11]1C=CC=C[CH:12]=1)[OH:10].BrCCCO.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)[C@H](C1C=CC=CC=1)O.C[C@H]1CCCNC1>O1CCCC1>[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:12][CH2:11][CH2:9][OH:10])[CH2:3]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 66784333HCID 66784333, compoundHCID 131727424HCID 131727424, compound

Product 1

HCID 28351514HCID 28351514, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3S)-3-methyl-piperidine/(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 tetrahydrofuran (200 mL), and heated under reflux for 30 hours. The insoluble matter was filtered off, the filtrate was concentrated, and ethyl acetate and hexane were added to the residue. The insoluble matter produced was filtered off, the filtrate was concentrated and the target substance (9.6 g, 85%) was obtained as a colorless oily material by distillation under reduced pressure. (3S)-3-methyl-piperidine (S)-(+)-mandelate was manufactured by the method described in the literature (J. Org. Chem., 1987, Vol. 52, p. 5466).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 hours
  3. filtrationThe insoluble matter was filtered off
  4. concentrationthe filtrate was concentrated
  5. additionethyl acetate and hexane were added to the residue
  6. customThe insoluble matter produced
  7. filtrationwas filtered off
  8. concentrationthe filtrate was concentrated
  9. customthe target substance (9.6 g, 85%) was obtained as a colorless oily material by distillation under reduced pressure

Sources & evidence

ORD record
ord-60cf84ea582a4ee8a648b56ccc86a186
Source dataset
uspto-grants-2009_04
Patent number
US07521455B2

Reaction notes

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