10,11-dihydro-5H-dibenzo(a,d)cycloheptene → 1-[2-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine

HRID 2308845Notes

Reaction equation

HRID 2308845 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C([Li])CCC.Cl[CH2:22][CH2:23][N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>O1CCCC1.CCCCCC>[CH: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]([CH2:22][CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 7002910,11-dihydro-5H-dibenzo(a,d)cyclohepteneHCID 816691-(2-Chloroethyl)pyrrolidineHCID 178418339Butyllithium

Product 1

HCID 201879311-[2-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

1.0 g of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene in 25 ml of dry tetrahydrofuran is treated dropwise at -70° with 6.8 ml of an about 1.14M solution of n-butyl lithium in hexane. The mixture is stirred at -70° for 60 minutes. There are subsequently added dropwise thereto at -30° 1.1 g of 2-chloroethylpyrrolidine in 2.5 ml of dry tetrahydrofuran and the mixture is stirred at -30° for 1 hour and at 0° to 5° for 3 hours. After evaporation of the mixture, the residue remaining is dissolved in toluene and washed with water. The organic phase is filtered over 10 g of aluminum oxide (activity grade II, neutral) using toluene for the elution. Crude 1-[2-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine is obtained as a yellow oil.

Workup

  1. additionThere are subsequently added dropwise
  2. customAfter evaporation of the mixture
  3. dissolutionthe residue remaining is dissolved in toluene
  4. washwashed with water
  5. filtrationThe organic phase is filtered over 10 g of aluminum oxide (activity grade II, neutral)
  6. washfor the elution

Sources & evidence

ORD record
ord-d45284d2ade6430f9722521173cea9ff
Source dataset
uspto-grants-1987_09
Patent number
US04691040

Reaction notes

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