Reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[CH3:13])[CH2:9][CH2:8][CH2:7]2.C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:31][C:32](Cl)=[O:33])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]>C1C=CC=CC=1>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:31][C:32]([NH:1][CH2:2][CH2:3][C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][C:12]=2[CH3:13])[CH2:9][CH2:8][CH2:7]3)=[O:33])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]Participants
Procedure
5-Aminoethyl-6-methylindan (4.0 g, 0.029 mole) was dissolved in 100 ml of dry benzene, 4 ml of triethylamine was added and a solution of the previously prepared 3,4-dimethoxyphenylacetyl chloride in dry benzene was added to the substituted indan mixture. The reaction mixture was refluxed for several hours and then gently heated overnight at a temperature below reflux. The reaction was then cooled, washed with 3×100 ml of 20% HCl solution, 3×100 ml of 8% NaHCO3 solution and 2×125 ml of water. The benzene layer was then reduced in volume on a rotary evaporator to yield a solid precipitate. The solid was filtered, washed with benzene, air dried to yield a slightly pink powder (3.5 g, mp 144°-145° C.). The crude product was then recrystallized from benzene (large volume), mp 144°-144.5° C.
Workup
- temperatureThe reaction mixture was refluxed for several hours
- temperaturegently heated overnight at a temperature below reflux
- temperatureThe reaction was then cooled
- washwashed with 3×100 ml of 20% HCl solution, 3×100 ml of 8% NaHCO3 solution and 2×125 ml of water
- customThe benzene layer was then reduced in volume on a rotary evaporator
- customto yield a solid precipitate
- filtrationThe solid was filtered
- washwashed with benzene, air
- customdried
Sources & evidence
- ORD record
- ord-663cc495f71a4c84924194f9d7641ca3
- Source dataset
- uspto-grants-1980_11
- Patent number
- US04232014
Linked notes
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