Maleic Acid → 1-[2-(4,5,10,11-tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine maleate

HRID 2308841Notes

Reaction equation

HRID 2308841 reaction equation
[CH2:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[C:5]=2[CH2:4][CH:3]=[CH:2]1.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]\[C:26]([OH:28])=[O:27]>CC(C)=O.CCCCCC>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]\[C:26]([OH:28])=[O:27].[CH2:12]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]([CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[C:7]=2[CH2:15][CH:14]=[CH:13]1

Participants

5

Reactant 2

HCID 444266Maleic AcidHCID 201879291-[2-(4,5,10,11-tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine

Product 1

HCID 704321281-[2-(4,5,10,11-tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine maleate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8058HexaneSolvent

Procedure

660 g of crude 1-[2-(4,5,10,11-tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine are dissolved in 3.0 l of acetone under an argon atmosphere while warming slightly (to about 40°). The solution obtained is cooled to about 10° and treated while stirring with a solution, pre-cooled to about 10°, of 264.0 g of maleic acid in 1.6 l of acetone and diluted with 4.0 l of n-hexane while passing argon through the mixture. After 15 hours at room temperature and with the exclusion of light, the resulting crystal slurry is filtered under suction, washed twice with 1.0 l of petroleum ether each time and dried at room temperature in a vacuum drying oven for 20 hours. There is obtained 1-[2-(4,5,10,11-tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine maleate of melting point 127°-129°. By concentration of the mother liquor to about 1 l there is obtained a section portion of melting point 123° -125°.

Workup

  1. temperaturewhile warming slightly (to about 40°)
  2. customThe solution obtained
  3. temperatureis cooled to about 10°
  4. additiontreated
  5. filtrationwith the exclusion of light, the resulting crystal slurry is filtered under suction
  6. washwashed twice with 1.0 l of petroleum ether each time
  7. customdried at room temperature in a vacuum
  8. customdrying oven for 20 hours

Sources & evidence

ORD record
ord-10b438af9c014bd2952d784baecf0f02
Source dataset
uspto-grants-1987_09
Patent number
US04691040

Reaction notes

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