HCID 23346464, compound → HCID 23346448, compound

HRID 1856280Notes

Reaction equation

HRID 1856280 reaction equation
Br[CH2:2][CH:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=1)[OH:4].C1(=O)[NH:22]C(=O)C2=CC=CC=C12.[K]>CN(C)C=O.O>[NH2:22][CH2:2][CH:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=1)[OH:4]

Participants

5

Reactant 2

HCID 23346464HCID 23346464, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 23346448HCID 23346448, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Crude 2-bromo-1-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol (7.3 g; prepared as described in Example 3) in dimethylformamide (100 g) is stirred at 40° C. for 4 hours with potassium phthalimide (5.0 g), then diluted with water and extracted three times with chloroform. The combined extracts are dried and evaporated to dryness. The crude 2-phthalimido-1-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol is added to ethanol (100 ml) containing hydrazine hydrate (1.5 g). The reaction mixture is stirred under reflux for 4 hours, concentrated hydrochloric acid (2 ml) is added, and the mixture is heated for 15 minutes. The solution is cooled, filtered from the solid precipitate and concentrated to a small volume. The concentrate is made alkaline with 2 N sodium hydroxide solution and repeatedly extracted with diethyl ether. Evaporation of the ether and crystallization of the residual product from cyclohexane gives 2-amino-1-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol, m.p. 76°-78° C.

Workup

  1. extractionextracted three times with chloroform
  2. customThe combined extracts are dried
  3. customevaporated to dryness
  4. additionThe crude 2-phthalimido-1-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol is added to ethanol (100 ml)
  5. additioncontaining hydrazine hydrate (1.5 g)
  6. temperatureunder reflux for 4 hours
  7. additionconcentrated hydrochloric acid (2 ml) is added
  8. temperaturethe mixture is heated for 15 minutes
  9. temperatureThe solution is cooled
  10. filtrationfiltered from the solid precipitate
  11. concentrationconcentrated to a small volume
  12. extractionrepeatedly extracted with diethyl ether
  13. customEvaporation of the ether and crystallization of the residual product from cyclohexane

Sources & evidence

ORD record
ord-cf0ab5442ef845449e705d01229802b7
Source dataset
uspto-grants-1980_08
Patent number
US04218472

Reaction notes

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