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

HRID 1981200Notes

Reaction equation

HRID 1981200 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[CH:6]([CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-].[Li+].C(=O)=O.CN>[Pt]>[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

6

Reactant 4

HCID 280Carbon Dioxide2×HCID 6329MethylamineHCID 433294Lithium ChlorideHCID 201879311-[2-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

2.0 g of 1-[2-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine and 2.5 g of lithium chloride are placed in a 100 ml glass vessel having a removable cover with 5 ground openings and fitted with a dry-ice condenser, thermometer, platinum sheet anode and cathode (each 2.5×2.5 cm, distance 2 cm). Subsequently, nitrogen is conducted through the apparatus for 20 minutes, the receiver is placed in a dry-ice/alcohol bath, the dry-ice condenser is charged with dry-ice and 70 g of methylamine are distilled directly into the apparatus from a pressure flask while stirring with a magnetic stirrer. Subsequently, a current of 2 amperes is applied, whereupon a voltage of 44 volts occurs and the cathode immediately becomes deep blue in color. The temperature is held at -10°. After a throughput of an amount of current of 3000 amperes (corresponding to 230% of the theoretical amount of current required for the complete conversion), the current is turned off and the solution is evaporated at 50° and under a slight vacuum. The residue is digested in hexane for a few minutes in an ultrasound bath. After filtration and evaporation, there is obtained crude 1-[2-(4,5,10,11-tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine which is purified in analogy to the details in Examples 1(j) to 1(l).

Workup

  1. customfitted with a dry-ice condenser
  2. customthe receiver is placed in a dry-ice/alcohol bath
  3. distillationare distilled directly into the apparatus from a pressure flask
  4. customis held at -10°
  5. customthe solution is evaporated at 50° and under a slight vacuum
  6. waitThe residue is digested in hexane for a few minutes in an ultrasound bath
  7. filtrationAfter filtration and evaporation

Sources & evidence

ORD record
ord-76362b601d5a471ab4c17f22cc577ca1
Source dataset
uspto-grants-1985_04
Patent number
US04513002

Reaction notes

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