Trifluoroacetic acid → 4-[3-[4-[(2-Benzothiazolyl)carbonyl]-1-piperidinyl]propoxy]benzoic acid methyl ester

HRID 1736438Notes

Reaction equation

HRID 1736438 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.I[CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O.O1CCCC1>[CH3:37][O:36][C:34](=[O:35])[C:33]1[CH:38]=[CH:39][C:30]([O:29][CH2:28][CH2:27][CH2:26][N:15]2[CH2:16][CH2:17][CH:12]([C:10]([C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[O:11])[CH2:13][CH2:14]2)=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 152370094-(Benzthiazole-2-carbonyl)piperidineHCID 153374624-(3-Iodopropoxy)benzoic acid, methyl ester

Product 1

HCID 153374634-[3-[4-[(2-Benzothiazolyl)carbonyl]-1-piperidinyl]propoxy]benzoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix (2-benzothiazolyl)(4-piperidinyl)methanone.CF3CO2H (7.08 g, 19.7 mmol), 4-(3-iodopropoxy)benzoic acid, methyl ester (6.50 g, 20.3 mmol), sodium hydrogen carbonate (3.41 g, 40.6 mmol), tetrahydrofuran (100 mL) and water (20 mL). Heat at reflux under an argon atmosphere overnight. Cool to room temperature, dilute with ethyl acetate (150 mL), wash with 10% sodium hydrogen carbonate (50 mL), water (2×50 mL) and saturated sodium chloride (50 mL). Dry (MgSO4), evaporate the solvent in vacuo and triturate with hexane. Collect the solid by filtration and recrystallize (methanol) to give the title compound as a pale yellow solid; mp 108°-109.5° C.

Workup

  1. temperatureHeat
  2. temperatureat reflux under an argon atmosphere overnight
  3. washwash with 10% sodium hydrogen carbonate (50 mL), water (2×50 mL) and saturated sodium chloride (50 mL)
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customtriturate with hexane
  7. customCollect the solid
  8. filtrationby filtration
  9. customrecrystallize (methanol)

Sources & evidence

ORD record
ord-9a8767047be04c28a4e00d82727f1936
Source dataset
uspto-grants-1996_07
Patent number
US05541200

Reaction notes

Loading…