Hydrochloric Acid → HCID 15337461, compound

HRID 1598778Notes

Reaction equation

HRID 1598778 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11].C(C(O)=O)(F)(F)F.Br[CH2:26][C:27]([O:29][CH3:30])=[O:28].C(=O)(O)[O-].[Na+].Cl>C(O)C.C(OCC)C.O.O1CCCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH2:14][CH2:13]1)=[O:11]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 60984Methyl bromoacetateHCID 516892Sodium BicarbonateHCID 152370094-(Benzthiazole-2-carbonyl)piperidine

Product 1

HCID 15337461HCID 15337461, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21585056Diethyl ether ethanolSolvent

Procedure

Mix (2-benzothiazolyl)(4-piperidinyl)methanone.CF3CO2H (3.0 g, 8.33 mmol), methyl bromoacetate (1.34 g, 8.74 mmol), sodium bicarbonate (1.75 g, 20.83 mmol), tetrahydrofuran (120 mL) and water (30 mL). Heat at reflux for 4 hours, cool to room temperature and partition between ethyl acetate and water. Separate the organic phase and extract the aqueous phase with ethyl acetate. Combine the organic phases, wash with water and dry (MgSO4). Evaporate the solvent in vacuo to give a yellow oil. Dissolve the oil in ethanol/ethyl ether and treat with ethereal hydrogen chloride gas. Cool overnight, collect the resulting solid by filtration, wash with ethyl ether and dry to give the title compound as a white crystalline solid; mp 177°-178° C.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 4 hours
  3. custompartition between ethyl acetate and water
  4. customSeparate the organic phase
  5. extractionextract the aqueous phase with ethyl acetate
  6. washwash with water
  7. dry with materialdry (MgSO4)
  8. customEvaporate the solvent in vacuo
  9. customto give a yellow oil
  10. temperatureCool overnight
  11. customcollect the resulting solid
  12. filtrationby filtration
  13. washwash with ethyl ether
  14. customdry

Sources & evidence

ORD record
ord-fa080e28e0f645078f4cc46d4032ca6a
Source dataset
uspto-grants-1998_04
Patent number
US05739150

Reaction notes

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