Piperidine → HCID 42598820, compound

HRID 875263Notes

Reaction equation

HRID 875263 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC1C=CC(S(O[CH2:18][C:19]2([OH:36])[C:23](=[O:24])[O:22][C@H:21]3[C:25]4[C@@:30]([CH3:33])([CH2:31][CH2:32][C:20]23[OH:35])[CH2:29][CH2:28][CH2:27][C:26]=4[CH3:34])(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(O)C>[OH:36][C:19]1([CH2:18][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:23](=[O:24])[O:22][C@H:21]2[C:25]3[C@@:30]([CH3:33])([CH2:31][CH2:32][C:20]12[OH:35])[CH2:29][CH2:28][CH2:27][C:26]=3[CH3:34]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 42598818HCID 42598818, compound

Product 1

HCID 42598820HCID 42598820, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Piperidine (70.59 mg, 0.829 mmol) was added to compound of example 5 (180 mg, 0.412 mmol) dissolved in ethanol (5 mL) and reaction mixture was stirred for 24 hours. Saturated sodium bicarbonate solution was added, and reaction mixture was extracted with dichloromethane (3×50 mL). Dichloromethane layer was washed with water and brine and was dried over sodium sulfate. Solvent was removed and the crude product was purified by column chromatography (silica gel, 5-10% ethyl acetate in petroleum ether) to obtain the title compound.

Workup

  1. customreaction mixture
  2. customreaction mixture
  3. extractionwas extracted with dichloromethane (3×50 mL)
  4. washDichloromethane layer was washed with water and brine
  5. dry with materialwas dried over sodium sulfate
  6. customSolvent was removed
  7. customthe crude product was purified by column chromatography (silica gel, 5-10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-c1863e25ae0e496db7eca769ffb7a945
Source dataset
uspto-grants-2015_03
Patent number
US08981131B2

Reaction notes

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