Water → HCID 11346343, compound

HRID 1978013Notes

Reaction equation

HRID 1978013 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1.C(N(CC)CC)C.[CH:23]1([C:26](Cl)=[O:27])[CH2:25][CH2:24]1.O>C1COCC1>[CH:23]1([C:26]([NH:1][CH2:2][CH2:3][CH:4]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=3)[CH2:7][CH2:6][CH2:5]2)=[O:27])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 21996472HCID 21996472, compound

Product 1

HCID 11346343HCID 11346343, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1,2,3,4-tetrahydro-7-methoxy-1-naphthylidene)acetonitrile (1.0 g, 5.02 mmol) in ethanol (10 ml) were added a saturated ammonia/ethanol solution (5 ml) and Raney nickel (W-2, 1 g). The mixture was stirred for 4 hours at 50° C. under hydrogen atmosphere (3-4 kgf/cm2). The Raney nickel was filtered off and, then, the solvent was distilled off under reduced pressure to give 1-(2-aminoethyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene. To a solution of this 1-(2-aminoethyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene and triethylamine (0.76 g, 7.53 mmol) in THF (20 ml) was gradually added dropwise, under ice-cooling, cyclopropanecarbonyl chloride (0.63 g, 6.02 mmol). The mixture was stirred for 30 minutes at room temperature. The reaction mixture was poured into water. The organic layer was subjected to extraction with chloroform. The extract solution was washed with brine and water, which was then dried over anhydrous magnesium sulfate, followed by distilling off the solvent. The residue was purified by means of a silica gel column chromatography (ethyl acetate:hexane=2:8) to give the above-titled compound (1.04 g, yield 76%, oil).

Workup

  1. temperaturecooling
  2. extractionThe organic layer was subjected to extraction with chloroform
  3. washThe extract solution was washed with brine and water, which
  4. dry with materialwas then dried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent
  6. customThe residue was purified by means of a silica gel column chromatography (ethyl acetate:hexane=2:8)

Sources & evidence

ORD record
ord-06c00a30ae234fa9950927ab90c05384
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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