Pyridine → HCID 58817650, compound

HRID 501293Notes

Reaction equation

HRID 501293 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[S:17][CH:18]=[CH:19][C:20]=2[Br:21])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:23][OH:24].N1C=CC=CC=1>O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[S:17][CH:18]=[CH:19][C:20]=2[Br:21])=[N:23][OH:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 58817522HCID 58817522, compound

Product 1

HCID 58817650HCID 58817650, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Stir a mixture of 4-(3-bromo-thiophene-2-carbonyl)-piperidine-1-carboxylic acid tert-butyl ester (Example 21a) (41.5 g, 0.11 mol), hydroxylamine hydrochloride (15.4 g, 0.23 mol) and pyridine (190 mL) at ambient temperature overnight. Pour the reaction into water (500 mL) and extract with dichloromethane (3 times). Wash the combined extracts with saturated CuSO4 solution (2 times), dry (MgSO4) and concentrate to a green solid. Dissolve the solid in toluene (175 mL) and let stand at ambient temperature for 3 h. Collect the resulting crystals that form and wash with toluene (60 mL). Concentrate the filtrate and again dissolve the residue in toluene and proceed to collect additional crystals to obtain a total yield of 25 g (58%) of the title compound as a light, green solid.

Workup

  1. additionPour
  2. extractionextract with dichloromethane (3 times)
  3. washWash the combined extracts with saturated CuSO4 solution (2 times)
  4. dry with materialdry (MgSO4)
  5. concentrationconcentrate to a green solid
  6. dissolutionDissolve the solid in toluene (175 mL)
  7. customCollect the resulting crystals that form
  8. washwash with toluene (60 mL)
  9. concentrationConcentrate the filtrate
  10. dissolutionagain dissolve the residue in toluene
  11. customto collect additional crystals

Sources & evidence

ORD record
ord-3ed8f90b2f8a4b80b94bd27c6cfea551
Source dataset
uspto-grants-2010_08
Patent number
US07772252B2

Reaction notes

Loading…