Triethylamine → 4-(4'-Ketopiperidinyl)butylphthalimide

HRID 962731Notes

Reaction equation

HRID 962731 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.Br[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:25]=[CH:24][CH:23]=[C:17]2[C:18]([NH:20][C:21](=[O:22])[C:16]=12)=[O:19].C(N(CC)CC)C>C(Cl)(Cl)Cl>[O:9]=[C:6]1[CH2:7][CH2:8][N:3]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:25]=[CH:24][CH:23]=[C:17]3[C:18]([NH:20][C:21](=[O:22])[C:16]=23)=[O:19])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723901PiperonylamineHCID 21960043Bromobutylphthalimide

Product 1

HCID 190858404-(4'-Ketopiperidinyl)butylphthalimideYield 21.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-piperidone hydrochloride hydrate (2 gram, 13 mmol), bromobutylphthalimide (3.67 gram, 13 mmol) and triethylamine (3.4 ml, 26 mmol) in Chloroform (25 ml) was refluxed overnight. The reaction mixture was washed with sat. NaHCO3 and was dried over Na2SO4. Purification using flash chromatography gave 4-(4'-ketopiperidinyl)butylphthalimide (0.85 gram).

Workup

  1. washThe reaction mixture was washed with sat. NaHCO3
  2. dry with materialwas dried over Na2SO4
  3. customPurification

Sources & evidence

ORD record
ord-0bfb102f7b9d429b861ae4a0bdcebcee
Source dataset
uspto-grants-1998_06
Patent number
US05760054

Reaction notes

Loading…