Hydrochloric Acid → 2-Cycloheptylaminoethylfluorene

HRID 256625Notes

Reaction equation

HRID 256625 reaction equation
[CH:1]1([NH:8][C:9]([CH2:11][C:12]2[CH:24]=[CH:23][C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15][C:14]=3[CH:13]=2)=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.Cl.[OH-].[Na+]>O1CCCC1.C(Cl)(Cl)Cl>[CH:1]1([NH:8][CH2:9][CH2:11][C:12]2[C:13]3[CH2:14][C:15]4[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:21]=3[CH:22]=[CH:23][CH:24]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 199361232-Cycloheptylcarbamoylmethylfluorene

Product 1

HCID 199361182-CycloheptylaminoethylfluoreneYield 66%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In dry tetrahydrofuran (30 ml) was dissolved 2-cycloheptylcarbamoylmethylfluorene (1.9 g) followed by dropwise addition of borane-methyl sulfide complex (1.8 ml) with ice-cooling. The mixture was then refluxed for 4 hrs, at the end of which time methanol (0.72 ml) was added with ice-cooling. The mixture was stirred at room temperature for 30 minutes, followed by addition of concentrated hydrochloric acid (1.8 ml) with ice-cooling. The mixture was refluxed again for 30 minutes. The reaction mixture was then cooled with ice and the resulting solid was recovered by filtration and washed with ether. The solid matter thus obtained was dissolved in chloroform and the solution was alkalinized with aqueous sodium hydroxide solution. The chloroform layer was taken and dried and the solvent was distilled off under reduced pressure to give 2-cycloheptylaminoethylfluorene (1.2 g).

Workup

  1. additionfollowed by dropwise addition of borane-methyl sulfide complex (1.8 ml) with ice-
  2. temperaturecooling
  3. additionwas added with ice-
  4. temperaturecooling
  5. temperaturecooling
  6. temperatureThe mixture was refluxed again for 30 minutes
  7. temperatureThe reaction mixture was then cooled with ice
  8. filtrationthe resulting solid was recovered by filtration
  9. washwashed with ether
  10. customThe solid matter thus obtained
  11. customdried
  12. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-786ed028652641f1a0dc880604df961e
Source dataset
uspto-grants-1993_11
Patent number
US05258405

Reaction notes

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