Hydrochloric Acid → (9H-Fluoren-9-yl)methyl 4-hydrazinylpiperidine-1-carboxylate hydrochloride

HRID 1699226Notes

Reaction equation

HRID 1699226 reaction equation
CC(C)(OC([NH:7][NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH:19]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:25]3[C:20]2=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:16])[CH2:11][CH2:10]1)=O)C.[ClH:33]>FC(F)(F)C(O)=O.C(OCC)(=O)C>[ClH:33].[CH:30]1[C:31]2[CH:19]([CH2:18][O:17][C:15]([N:12]3[CH2:13][CH2:14][CH:9]([NH:8][NH2:7])[CH2:10][CH2:11]3)=[O:16])[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]=2[CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 15606373(9H-Fluoren-9-yl)methyl 4-(2-(tert-butoxycarbonyl)hydrazinyl)piperidine-1-carboxylate

Product 1

HCID 18321221(9H-Fluoren-9-yl)methyl 4-hydrazinylpiperidine-1-carboxylate hydrochloride

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

21.8 g (0.0498 mol) of N-(1,1-dimethylethoxycarbonyl)-N′-[1-(9H-fluoren-9-ylmethoxycarbonyl)-4-piperidinyl]-hydrazine were dissolved in 100 ml of trifluoroacetic acid and stirred for 1 hour at room temperature. The excess trifluoroacetic acid was removed in vacuo, the residue was dissolved in 50 ml of water and made alkaline with 10% aqueous sodium carbonate solution. The solution was extracted thoroughly with dichloromethane, the combined extracts were dried over magnesium sulphate and evaporated down in vacuo. The residue thus obtained was taken up in ethyl acetate and converted into the hydrochloride by the addition of ethereal hydrogen chloride solution. After recrystallisation from anhydrous ethanol 6.2 g (33.3% of theory) of colourless crystals of melting point 160-162° C. were obtained.

Workup

  1. customThe excess trifluoroacetic acid was removed in vacuo
  2. dissolutionthe residue was dissolved in 50 ml of water
  3. extractionThe solution was extracted thoroughly with dichloromethane
  4. dry with materialthe combined extracts were dried over magnesium sulphate
  5. customevaporated down in vacuo
  6. customThe residue thus obtained
  7. customAfter recrystallisation from anhydrous ethanol 6.2 g (33.3% of theory) of colourless crystals of melting point 160-162° C.
  8. customwere obtained

Sources & evidence

ORD record
ord-09adfbc0ffcc401dae8ae843f0f7a9ec
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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