Succinic anhydride → 1-(4-oxo-4-morpholinobutyryl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine

HRID 1584169Notes

Reaction equation

HRID 1584169 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[C:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:22]1(=[O:28])[O:27][C:25](=O)[CH2:24][CH2:23]1.C(N(CC)CC)C.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[O:27]=[C:25]([N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1)[CH2:24][CH2:23][C:22]([N:19]1[CH2:18][CH2:17][C:16](=[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9]=[CH:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)[CH2:21][CH2:20]1)=[O:28]

Participants

7

Reactant 5

HCID 7922Succinic anhydrideHCID 8083MorpholineHCID 8471TriethylamineHCID 1597184-(5H-Dibenzo(a,d)cyclohepten-5-ylidene)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 212240751-(4-oxo-4-morpholinobutyryl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 50 ml of dichloromethane, 4-(5H-dibenzo [a,d]cyclohepten-5-ylidene)piperidine (0.27 g, 1.0 mmol), succinic anhydride (0.12 g, 1.2 mmol), and triethylamine (0.17 ml, 1.2 mmol) were stirred at room temperature overnight. Morpholine (0.14 ml, 1.6 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.27 g, 1.4 mmol) were added and the mixture was further stirred at room temperature for 8 hours. The reaction mixture was washed with 30 ml of 1 N hydrochloric acid, 30 ml of a 1 N aqueous sodium hydroxide solution, and 30 ml of a saturated aqueous sodium chloride solution, dried over magnesium sulfate powder, and purified by silica gel chromatography to obtain the titled compound. Amount obtained: 0.44 g (1.0 mol); Yield: 100%

Workup

  1. washThe reaction mixture was washed with 30 ml of 1 N hydrochloric acid, 30 ml of a 1 N aqueous sodium hydroxide solution, and 30 ml of a saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate powder
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-783ffd7bfea143459b933888e7d81eb0
Source dataset
uspto-grants-1999_08
Patent number
US05932593

Reaction notes

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