Piperidin-4-ol → HCID 86682307, compound

HRID 1055235Notes

Reaction equation

HRID 1055235 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C[O:9][C:10](=O)[CH2:11][C:12](=[O:15])[CH2:13][CH3:14]>>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:10](=[O:9])[CH2:11][C:12](=[O:15])[CH2:13][CH3:14])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 79341Piperidin-4-olHCID 121699Methyl 3-oxovalerate

Product 1

HCID 86682307HCID 86682307, compound

Procedure

59.0 g (583 mmol) of 4-hydroxypiperidine and 79.7 g (612 mmol) of 3-oxovaleric acid methyl ester were heated for 9 h at 110° C., and the resulting methanol was removed via a distillation bridge. The reaction residue was freed from volatiles on a rotary evaporator, taken up in ethanol, and filtered through 600 ml of strongly acidic ion exchanger (Dowex® HCR-W2), concentrated again and purified by column chromatography (silica gel, eluent's gradient from ethyl acetate to ethanol). The pure product fractions were freed from solvent on a rotary evaporator and yielded 63.6 g (55%) of a viscous, clear, colorless oil.

Workup

  1. customthe resulting methanol was removed via a distillation bridge
  2. customThe reaction residue was freed from volatiles on a rotary evaporator
  3. filtrationfiltered through 600 ml of strongly acidic ion exchanger (Dowex® HCR-W2)
  4. concentrationconcentrated again
  5. custompurified by column chromatography (silica gel, eluent's gradient from ethyl acetate to ethanol)
  6. customThe pure product fractions were freed from solvent on a rotary evaporator
  7. customyielded 63.6 g (55%) of a viscous, clear, colorless oil

Sources & evidence

ORD record
ord-d8ac812f41214e26b1f4b6e4c004b8f2
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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