Water → HCID 86663678, compound

HRID 423599Notes

Reaction equation

HRID 423599 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CS(O[CH:14]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:18][CH2:17]1)[CH3:15])(=O)=O.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH:14]([CH:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])[CH2:20][CH2:21]2)[CH3:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27628652-Bromo-5-hydroxypyridineHCID 86638743HCID 86638743, compound

Product 1

HCID 86663678HCID 86663678, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-bromo-3-pyridinol (0.31 g, 1.78 mmol), (±)-phenylmethyl 4-{1-[(methylsulfonyl)oxy]ethyl}-1-piperidinecarboxylate (0.73 g, 2.14 mmol) and K2CO3 (0.50 g, 3.57 mmol) in DMF (12 mL) was stirred at ambient temperature for 30 min, then heated at 70° C. overnight, then heated at 100° C. for 27 h. The mixture was cooled to ambient temperature and poured into water, and extracted with EtOAc (60 mL×2). The combined organic extract was washed with water, brine and dried over Na2SO4, filtered, and the filtrate was concentrated to give crude (±)-phenylmethyl 4-{1-[(6-bromo-3-pyridinyl)oxy]ethyl}-1-piperidinecarboxylate as a brown oil, which was used without further purification.

Workup

  1. temperatureheated at 70° C. overnight
  2. temperatureheated at 100° C. for 27 h
  3. temperatureThe mixture was cooled to ambient temperature
  4. extractionextracted with EtOAc (60 mL×2)
  5. extractionThe combined organic extract
  6. washwas washed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2cd7c18606cd46a7907a4403ee80e51e
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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