Water → 2-Di-n-propylamino-8-methoxyacetyl-1,2,3,4-tetrahydronaphthalene

HRID 129931Notes

Reaction equation

HRID 129931 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([Sn](C)(C)C)[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].[CH3:22][O:23][CH2:24][C:25](Cl)=[O:26].O>C1C=CC=CC=1>[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:25](=[O:26])[CH2:24][O:23][CH3:22])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 96623Methoxyacetyl chlorideHCID 194270892-Dipropylamino-8-trimethylstannyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 152335382-Di-n-propylamino-8-methoxyacetyl-1,2,3,4-tetrahydronaphthaleneYield 98.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Bis-triphenylphosphine palladium dichloride (120 mg) was added to a solution of 2-dipropylamino-8-trimethylstannyl-1,2,3,4-tetrahydronaphthalene (500 mg, 1.27 mmol) in benzene (20 ml). Methoxyacetyl chloride (1.5 ml; 1.77 g; 16.5 mmol) was added. The reaction mixture was stirred at room temperature overnight and then heated to reflux for 5 hr. The reaction mixture was poured into water and extracted with methylene chloride. The extract was dried (MgSO4) and concentrated to give 800 mg of crude product. Purification by chromatography using 1:10 methanol: methylene chloride as solvent gave 380 mg of 2-di-n-propylamino-8-methoxyacetyl-1,2,3,4-tetrahydronaphthalene.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hr
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract was dried (MgSO4)
  5. concentrationconcentrated
  6. customto give 800 mg of crude product
  7. customPurification by chromatography

Sources & evidence

ORD record
ord-4f11af5383494e96afd32e0f12a82f08
Source dataset
uspto-grants-1995_11
Patent number
US05470977

Reaction notes

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