4-Nitrophthalic acid anhydride → 1-n-Butyl-4-(4-nitrophthalimido)piperidine

HRID 972816Notes

Reaction equation

HRID 972816 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:4][CH2:3]1.[N+:12]([C:15]1[CH:16]=[C:17]2[C:22](=O)[O:21][C:19](=[O:20])[C:18]2=[CH:24][CH:25]=1)([O-:14])=[O:13]>C(Cl)(Cl)Cl>[CH2:8]([N:5]1[CH2:6][CH2:7][CH:2]([N:1]2[C:22](=[O:21])[C:17]3=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:25][CH:24]=[C:18]3[C:19]2=[O:20])[CH2:3][CH2:4]1)[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 2309764-Nitrophthalic acid anhydrideHCID 122628201-Butylpiperidin-4-amine

Product 1

HCID 537449311-n-Butyl-4-(4-nitrophthalimido)piperidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4.69 Grams of 4-amino-1-n-butylpiperidine in 100 milliliters of chloroform were added to a suspension of 5.79 grams of 4-nitrophthalic anhydride in 75 milliliters of chloroform and the solution was evaporated to dryness. 40 Milliliters of acetic anhydride were added and the mixture was then heated on a steam bath for half an hour. The excess acetic anhydride was evaporated off and the residue dissolved in 40 milliliters of methanol and ethereal hydrogen chloride was added to give a solid which was collected giving 2.50 grams of the title compound as the monohydrochloride.

Workup

  1. customthe solution was evaporated to dryness
  2. addition40 Milliliters of acetic anhydride were added
  3. temperaturethe mixture was then heated on a steam bath for half an hour
  4. customThe excess acetic anhydride was evaporated off
  5. dissolutionthe residue dissolved in 40 milliliters of methanol
  6. additionethereal hydrogen chloride was added
  7. customto give a solid which
  8. customwas collected

Sources & evidence

ORD record
ord-d062ba32e1f64c5a8471b9811b6f7a75
Source dataset
uspto-grants-1977_10
Patent number
US04053615

Reaction notes

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