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

HRID 266088Notes

Reaction equation

HRID 266088 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 atomsphere 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 atomsphere 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-d7b589eda8d94e1d842355035f3ee71e
Source dataset
uspto-grants-1997_07
Patent number
US05650416

Reaction notes

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