1-Piperazinecarboxylic acid, ethyl ester → ethyl 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-piperazinecarboxylate

HRID 2290293Notes

Reaction equation

HRID 2290293 reaction equation
Cl[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.[N:17]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>CN(C)C=O>[CH:13]1[C:4]2[CH:5]=[CH:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH:2]([N:20]3[CH2:19][CH2:18][N:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:22][CH2:21]3)[C:3]=2[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 110751355-Chloro-5H-dibenzo[a,d][7]annulene

Product 1

HCID 13688013ethyl 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 gram (44 millimoles) of 5-chloro-5H-dibenzo-[a,d]cycloheptene prepared in a manner similar to that previously described was added to a solution of 1.4 grams of ethyl N-piperazinecarboxylate in 10 milliliters of dimethylformamide and the resulting mixture allowed to stir overnight at room temperature. At the end of this period, the mixture was subjected to reduced pressure to remove most of the dimethylformamide. Aqueous saturated sodium bicarbonate solution was added, mixed and then extracted with diethyl ether. The ether extract was washed with water and saturated sodium chloride solution, dried over magnesium sulfate, the dried solution subjected to reduced pressure to remove the ether and to obtain the ethyl 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-piperazinecarboxylate product as residue. The crude product was treated with and crystallized from acetonitrile. The product after several recrystallizations had a melting point of 159°-160° C. and elemental analyses as follows:

Workup

  1. customto remove most of the dimethylformamide
  2. additionAqueous saturated sodium bicarbonate solution was added
  3. additionmixed
  4. extractionextracted with diethyl ether
  5. extractionThe ether extract
  6. washwas washed with water and saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customto remove the ether

Sources & evidence

ORD record
ord-92c5c32bb01941deb7e94ad3815ab026
Source dataset
uspto-grants-1986_10
Patent number
US04616023

Reaction notes

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