Benzene → Kabi 2023

HRID 1856287Notes

Reaction equation

HRID 1856287 reaction equation
C(Cl)(Cl)=[O:2].[CH3:5][N:6]([C:8]([C:11]1[C:19]2[C:14](=CC=CC=2)[C:13]2([CH2:23][CH2:22][CH2:21][CH2:20]2)C=1)(O)C)C.[OH-].[K+].[CH:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C.O>[CH3:5][NH:6][CH2:8][CH:11]([C:19]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:13]2([CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:14]=1)[OH:2]

Participants

7

Reactant 4

HCID 241BenzeneHCID 6371PhosgeneHCID 14797Potassium HydroxideHCID 23346456HCID 23346456, compound

Product 1

HCID 192124Kabi 2023

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Phosgene (1 g) is added to dimethylamino-1-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol (2.9 g) in benzene (25 ml). The mixture is stirred at room temperature for 30 minutes and then under reflux for 2 hours. Evaporation of the solvent under reduced pressure gives an oil which crystallizes. Recrystallization from diisopropyl ether gives a pure product, m.p. 75°-77° C. This compound, 5-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol (2 g), is refluxed for 2 hours with a solution of potassium hydroxide (5 g) in ethanol (50 ml) and water (10 ml). Most of the solvent is evaporated under reduced pressure, water (25 ml) is added and the amine is extracted into chloroform. Drying and evaporation of the solvent gives the crystalline title compound, which after recrystallization from diisopropyl ether melts at 133°-134° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. customEvaporation of the solvent under reduced pressure
  3. customgives an oil which
  4. customcrystallizes
  5. customRecrystallization from diisopropyl ether
  6. customgives a pure product, m.p. 75°-77° C
  7. customMost of the solvent is evaporated under reduced pressure, water (25 ml)
  8. additionis added
  9. extractionthe amine is extracted into chloroform
  10. customDrying
  11. customevaporation of the solvent

Sources & evidence

ORD record
ord-d8be8dc967e442c8bdc8f4325e1a1c7c
Source dataset
uspto-grants-1980_08
Patent number
US04218472

Reaction notes

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