Triethylamine → HCID 14253325, compound

HRID 845436Notes

Reaction equation

HRID 845436 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[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:6](=[O:7])[C:5]4[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:37][CH2:38]3)[C:24]=2[CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 137534104-(5H-Dibenzo[a,d][7]annulen-5-yl)piperidine

Product 1

HCID 14253325HCID 14253325, compoundYield 106.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.64 gram (4.03 millimoles) of p-fluorobenzoyl chloride, 1.84 grams (18.2 millimoles) of triethylamine, 0.22 gram (1.82 millimoles) of 4-dimethylaminopyridine was added at ambient temperature to a solution of 1.00 gram (3.63 millimoles) of 4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine in 40 milliliters of dry methylene chloride while protected from atmospheric moisture and the mixture stirred for a total of about 50 minutes. About 10 grams of ice was added to the reaction mixture to quench the reaction and the resulting biphasic mixture stirred and allowed to warm to room temperature. The aqueous and organic phases were separated and the organic phase washed successively with 5 percent hydrochloric acid, aqueous bicarbonate and brine. The washed solution was dried over magnesium sulfate, the drying agent then filtered off and the solvent vaporized in vacuo to obtain 1.54 grams of 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-(p-fluorobenzoyl)piperidine residue which crystallized in a few hours at ambient temperature. Recrystallization from toluene produced white needles. The product had a melting point of 150°-151° C. Elemental analyses indicated presence of solvent of crystallization; the results calculated for 1 mole of toluene of crystallization were as follows:

Workup

  1. customto quench
  2. customthe reaction
  3. stirringthe resulting biphasic mixture stirred
  4. customThe aqueous and organic phases were separated
  5. washthe organic phase washed successively with 5 percent hydrochloric acid, aqueous bicarbonate and brine
  6. dry with materialThe washed solution was dried over magnesium sulfate
  7. filtrationthe drying agent then filtered off

Sources & evidence

ORD record
ord-2dc9ef2b7acb44c7ba1fc12b911f7abb
Source dataset
uspto-grants-1988_07
Patent number
US04758577

Reaction notes

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