Water → HCID 9948591, compound

HRID 1682580Notes

Reaction equation

HRID 1682580 reaction equation
[CH3:1][Li].[ClH:3].[C:4]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[CH2:15][CH:14]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH2:13][CH2:12]2)([OH:6])=O.O>CCOCC>[ClH:3].[C:4]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[CH2:15][CH:14]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH2:13][CH2:12]2)(=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 19044850HCID 19044850, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 9948591HCID 9948591, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 5% solution of methyl lithium in ether (0.6 ml, 0.96 mmol) was added to a chilled slurry of (±)-8-Carboxy-2-(dipropylamino)tetralin hydrochloride (100 mg, 0, 32 mmol) in ether. The mixture was stirred at room temperature and under nitrogen for three days. Water was added carefully and the mixture was extracted with ether. The organic layer was dried (potassium carbonate) and concentrated. The residue was purified by chromatography on an alumina column eluted with ether/light petroleum 1:4. The pure fractions were pooled, concentrated and converted into the hydrochloride. Recrystallization from acetonitrile/ether gave 55 mg (56%) of pure 8-acetyl-2-(dipropylamino)tetralin hydrochloride.

Workup

  1. extractionthe mixture was extracted with ether
  2. dry with materialThe organic layer was dried (potassium carbonate)
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on an alumina column
  5. washeluted with ether/light petroleum 1:4
  6. concentrationconcentrated
  7. customRecrystallization from acetonitrile/ether

Sources & evidence

ORD record
ord-799be45092084d52940af20036610225
Source dataset
uspto-grants-1997_06
Patent number
US05635537

Reaction notes

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