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

HRID 2308844Notes

Reaction equation

HRID 2308844 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[CH2:6][C:5]=2[CH2:4][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>[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]([CH2:22][CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:7]=2[CH2:15][CH:14]=[CH:13]1

Participants

6

Reactant 3

HCID 816691-(2-Chloroethyl)pyrrolidineHCID 201879321,4,10,11-tetrahydro-5H-dibenzo[a,d]cyclohepteneHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

1.0 g of 1,4,10,11-tetrahydro-5H-dibenzo[a,d]cycloheptene in 20 ml of dry tetrahydrofuran are treated dropwise at between -70° and -60° with 9.0 ml of an about 0.85M solution of n-butyl lithium in hexane. The mixture is stirred at -70° for 60 minutes and at -30° for 30 minutes, a solution of 2.1 g of 2-chloroethylpyrrolidine in 5 ml of dry tetrahydrofuran at -30° is added dropwise thereto and subsequently the mixture is stirred at -30° for an additional 30 minutes, at 0° to 5° for 3 hours and at room temperature for 30 minutes. After evaporation of the mixture, the residue remaining is dissolved in toluene and washed ion-free with water. The organic phase is filtered over aluminum oxide (activity grade II, neutral) using toluene for the elution. Crude 1-[2-(4,5,10,11-tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine is obtained.

Workup

  1. stirringsubsequently the mixture is stirred at -30° for an additional 30 minutes, at 0° to 5° for 3 hours and at room temperature for 30 minutes
  2. customAfter evaporation of the mixture
  3. dissolutionthe residue remaining is dissolved in toluene
  4. washwashed ion-free with water
  5. filtrationThe organic phase is filtered over aluminum oxide (activity grade II, neutral)
  6. washfor the elution

Sources & evidence

ORD record
ord-fde73a4343f3410792db3e7e556a2da5
Source dataset
uspto-grants-1987_09
Patent number
US04691040

Reaction notes

Loading…