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

HRID 1491684Notes

Reaction equation

HRID 1491684 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]([O:36][CH3:37])=[CH:32][CH:31]=1.[C:38](=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][CH2:38][C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)[CH2:14][CH2:13]1)=[O:11]

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 126856121-(3-Chloropropoxy)-4-methoxybenzeneHCID 152370094-(Benzthiazole-2-carbonyl)piperidine

Product 1

HCID 18930347[2-Benzothiazolyl][1-[3-(4-methoxyphenyl)propoxy]-4-piperidinyl]methanone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix (2-benzothiazolyl)(4-piperidinyl)methanone.CF3CO2H (7.0 g, 19.5 mmol), 1-(3-chloropropoxy)-4-methoxybenzene (4.01 g, 20.0 mmol), sodium bicarbonate (3.36 g, 40.0 mmol), sodium iodide (3.04 g, 20.3 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 an yellow solid Purify by chromatography (ethyl acetate) and recrystallize (ethanol) to give the title compound as a pale yellow solid; mp 114°-115° 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 an yellow solid
  7. customPurify by chromatography (ethyl acetate)
  8. customrecrystallize (ethanol)

Sources & evidence

ORD record
ord-1199605160ec4ffe8a130188bb9a58e4
Source dataset
uspto-grants-1994_12
Patent number
US05371093

Reaction notes

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