4-Nitrophthalic acid anhydride → 1-Cyclohexyl-4-(4-nitrophthalimido)piperidine

HRID 972818Notes

Reaction equation

HRID 972818 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[N+:14]([C:17]1[CH:18]=[C:19]2[C:24](=O)[O:23][C:21](=[O:22])[C:20]2=[CH:26][CH:27]=1)([O-:16])=[O:15]>C(Cl)(Cl)Cl>[CH:8]1([N:5]2[CH2:6][CH2:7][CH:2]([N:1]3[C:24](=[O:23])[C:19]4=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:27][CH:26]=[C:20]4[C:21]3=[O:22])[CH2:3][CH2:4]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 2309764-Nitrophthalic acid anhydrideHCID 47782391-Cyclohexylpiperidin-4-amine

Product 1

HCID 214055491-Cyclohexyl-4-(4-nitrophthalimido)piperidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6.85 Grams of 4-amino-1-cyclohexylpiperidine were added to 7.26 grams of 4-nitrophthalic anhydride in 100 milliliters of chloroform and the solution was evaporated to dryness. 50 millilters of acetic anhydride were then added and the solution was heated on a steam bath for half an hour. The excess acetic anhydride was evaporated off and the residue dissolved in 40 millilters of isopropyl alcohol and the product crystallised out. This was filtered, dried and dissolved in the least amount of ethanol and ethereal hydrogen chloride added to give 2.85 grams of the title compound which was collected as the monohydrochloride. Melting Point: 265°-270° C.

Workup

  1. customthe solution was evaporated to dryness
  2. addition50 millilters of acetic anhydride were then added
  3. temperaturethe solution was heated on a steam bath for half an hour
  4. customThe excess acetic anhydride was evaporated off
  5. dissolutionthe residue dissolved in 40 millilters of isopropyl alcohol
  6. customthe product crystallised out
  7. filtrationThis was filtered
  8. customdried
  9. dissolutiondissolved in the least amount of ethanol and ethereal hydrogen chloride
  10. additionadded

Sources & evidence

ORD record
ord-773fa9ea11ee4dd8a10393da312b47f3
Source dataset
uspto-grants-1977_10
Patent number
US04053615

Reaction notes

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