Water → 1-[2-(Acetylamino)ethyl]-6-methoxyindan

HRID 1978010Notes

Reaction equation

HRID 1978010 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23].O>ClCCl>[C:22]([NH:1][CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 110196681-(2-Aminoethyl)-6-methoxyindan

Product 1

HCID 155239391-[2-(Acetylamino)ethyl]-6-methoxyindanYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-aminoethyl)-6-methoxyindan (0.80 g, 4.18 mmol) and triethylamine (0.44 g, 4.39 mmol) in dichloromethane (15 ml) was gradually added dropwise, under ice cooling, acetyl chloride (0.33 g, 4.18 mmol). The mixture was stirred for 10 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 1N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and brine, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was recrystallized from ethyl acetate/isopropyl ether to give the above-titled compound (yield 0.68 g, 70%).

Workup

  1. extractionThe organic layer was subjected to extraction with chloroform
  2. washThe extract solution was washed with 1N hydrochloric acid
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and brine, which was dried over anhydrous magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-58034dd801ae4bb6b901e1e52cb8494d
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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