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

HRID 1683264Notes

Reaction equation

HRID 1683264 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. customdried (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-f5c4a8de6e1f4bf7be7ce7467dff5b2c
Source dataset
uspto-grants-1997_06
Patent number
US05637624

Reaction notes

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