Sodium Iodide → [2-Benzothiazolyl][1-[3-(4-acetamidophenyl)propoxy]-4-piperidinyl]methanone

HRID 1450428Notes

Reaction equation

HRID 1450428 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:18]([C:22]([OH:24])=O)(F)(F)F.ClCCCO[C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:39])[CH3:38])=[CH:32][CH:31]=1.[C:40](=O)(O)[O-].[Na+].[I-].[Na+]>C(OCC)(=O)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]([O:24][CH2:22][CH2:18][CH2:40][C:30]2[CH:31]=[CH:32][C:33]([NH:36][C:37](=[O:39])[CH3:38])=[CH:34][CH:35]=2)[CH2:14][CH2:13]1)=[O:11]

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 5147668N-[4-(3-chloropropoxy)phenyl]acetamideHCID 152370094-(Benzthiazole-2-carbonyl)piperidine

Product 1

HCID 18930370[2-Benzothiazolyl][1-[3-(4-acetamidophenyl)propoxy]-4-piperidinyl]methanone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix (2-benzothiazolyl)(4-piperidinyl)methanone.CF3CO2H (3.45 g, 9.6 mmol), 1-(3-chloropropoxy)-4-acetamidobenzene (2.20 g, 9.66 mmol), sodium bicarbonate (1.68 g, 20.0 mmol), sodium iodide (1.50 g, 10.0 mmol ), tetrahydrofuran (100 mL) and water (20 mL). Place under an argon atmosphere and heat at reflux for 24 hours. Dilute with ethyl acetate (100 mL) and wash with water (50 mL) and brine (50 mL). Dry (MgSO4), evaporate the solvent in vacuo to give a pale yellow solid. Purify by recrystallization (ethanol) to give the title compound as a pale yellow solid; mp 171°-172° C.

Workup

  1. temperaturePlace under an argon atmosphere and heat
  2. temperatureat reflux for 24 hours
  3. washwash with water (50 mL) and brine (50 mL)
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customto give a pale yellow solid
  7. customPurify by recrystallization (ethanol)

Sources & evidence

ORD record
ord-fdb1bab999254ac48ffe9df79b203ae9
Source dataset
uspto-grants-1997_02
Patent number
US05602147

Reaction notes

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