HCID 20256339, compound → HCID 86051552, compound

HRID 615627Notes

Reaction equation

HRID 615627 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][CH2:9]2.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K]>CN(C)C=O.C(Cl)Cl>[CH2:9]1[C:10]2[C:6](=[C:5]([O:4][CH2:3][CH2:2][N:18]3[C:14](=[O:24])[C:15]4[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:17]3=[O:19])[CH:13]=[CH:12][CH:11]=2)[CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 20256339HCID 20256339, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 86051552HCID 86051552, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 54.01 g (0.226 mole) of 4-(2-bromoethoxy) indan and 41.81 g (0.226 mole) of potassium phthalimide in 1200 ml of dimethylformamide was stirred overnight at 85° C. The reaction was filtered and dimethylformamide removed in vacuo in a rotary evaporator to give a white solid. The solid was dissolved in methylene chloride and extracted with water. Methylene chloride was evaporated to give a light brown solid. The solid was triturated with diethyl ether to give 59.3 g light brown solid. A portion of the solid was recrystallized from methylene chloride-ethanol-diethyl ether to give a white crystalline solid, m.p. 128.5°-132.0° C.

Workup

  1. filtrationThe reaction was filtered
  2. customdimethylformamide removed in vacuo in a rotary evaporator
  3. customto give a white solid
  4. extractionextracted with water
  5. customMethylene chloride was evaporated
  6. customto give a light brown solid
  7. customThe solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-2d45250f8cf545f29c9a3ddaee37dd94
Source dataset
uspto-grants-1985_02
Patent number
US04500529

Reaction notes

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