Ammonium Hydroxide → 2-Di-n-propylamino-8-methylsulfonyl-1,2,3,4-tetrahydronaphthalene

HRID 256566Notes

Reaction equation

HRID 256566 reaction equation
[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([S:15]([CH3:17])=[O:16])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].ClC1C=CC=C(C(OO)=[O:29])C=1.[NH4+].[OH-]>FC(F)(F)C(O)=O>[CH2:18]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([S:15]([CH3:17])(=[O:29])=[O:16])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 190432102-Dipropylamino-8-methylsulfinyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 190432112-Di-n-propylamino-8-methylsulfonyl-1,2,3,4-tetrahydronaphthaleneYield 30%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

To a solution of 2-dipropylamino-8-methylsulfinyl-1,2,3,4-tetrahydronaphthalene (350 mg, 1.19 mMol) in trifluoroacetic acid (20 ml) was added a solution of metachloroperbenzoic acid (80%, 518 mg, 2.38 mMol) in trifluoroacetic acid (5 mL). The solution was stirred at room temperature for 18 hours and poured over ice. The resulting mixture was made basic (NH4OH) and extracted well with dichloromethane. The organic extracts were combined, dried (Na2SO4) and concentrated in vacuo to give the crude title compound as a brown oil. Purification by flash chromatography (3% methanol in dichloromethane+tr. NH4OH) gave the desired product as a light orange oil (110 mg, 30%). The maleate salt was formed. Recrystallization (ethanol/diethyl ether) gave a colorless solid (70 mg, m.p.=113°-114° C.).

Workup

  1. additionpoured over ice
  2. extractionextracted well with dichloromethane
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give the crude title compound as a brown oil
  6. customPurification by flash chromatography (3% methanol in dichloromethane+tr. NH4OH)

Sources & evidence

ORD record
ord-71ab2ec3e9934332a751187df33a6dc9
Source dataset
uspto-grants-1993_11
Patent number
US05258379

Reaction notes

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