Glutaric anhydride → 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-delta-oxo-1-piperidinepentanoic acid

HRID 845435Notes

Reaction equation

HRID 845435 reaction equation
C(N(C(C)C)C(C)C)C.[C:10]1(=[O:17])[O:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11]1.[CH:18]1[C:28]2[CH:27]=[CH:26][C:25]3[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=3[CH:23]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[C:22]=2[CH:21]=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:29]1[C:25]2[CH:26]=[CH:27][C:28]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[CH:23]([CH:33]3[CH2:34][CH2:35][N:36]([C:14](=[O:15])[CH2:13][CH2:12][CH2:11][C:10]([OH:16])=[O:17])[CH2:37][CH2:38]3)[C:24]=2[CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 7940Glutaric anhydrideHCID 81531DiisopropylethylamineHCID 137534104-(5H-Dibenzo[a,d][7]annulen-5-yl)piperidine

Product 1

HCID 142533284-(5H-dibenzo[a,d]cyclohepten-5-yl)-delta-oxo-1-piperidinepentanoic acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.04 gram (0.36 millimole) of 4-dimethylaminopyridine, 0.94 gram (7.26 millimoles) of ethyl diisopropylamine, and 0.41 gram (3.63 millimoles) of glutaric anhydride were added successively to a solution of 1.00 gram (3.63 millimoles) of 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-piperidine and the resulting mixture stirred at ambient temperature for two hours. The reaction mixture was diluted with 100 milliliters of methylene chloride and washed with aqueous hydrochloric acid and then with brine. The washed solution was dried over magnesium sulfate, the drying agent filtered and the solution evaporated in vacuo whereupon a foam was produced which when triturated with hot acetonitrile produced white crystals. The crystals were recrystallized from hot acetic acid/acetonitrile to obtain 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-δ-oxo-1-piperidinepentanoic acid product, m.p. 180°-186° C. The product had elemental analyses as follows:

Workup

  1. washwashed with aqueous hydrochloric acid
  2. dry with materialThe washed solution was dried over magnesium sulfate
  3. filtrationthe drying agent filtered
  4. customthe solution evaporated in vacuo whereupon a foam
  5. customwas produced which when
  6. customtriturated with hot acetonitrile produced white crystals
  7. customThe crystals were recrystallized from hot acetic acid/acetonitrile

Sources & evidence

ORD record
ord-c42dab549b5941d09eae260fb4e34fd7
Source dataset
uspto-grants-1988_07
Patent number
US04758577

Reaction notes

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