Bromobenzene → HCID 12519354, compound

HRID 1395653Notes

Reaction equation

HRID 1395653 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li].BrC1C=CC=CC=1.[C:16]([CH:24]1[CH2:33][N:32]2[CH:27]([CH2:28][CH2:29][CH2:30][CH2:31]2)[CH2:26][CH2:25]1)(=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCOCC.O>[C:1]1([C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:24]2[CH2:33][N:32]3[CH:27]([CH2:28][CH2:29][CH2:30][CH2:31]3)[CH2:26][CH2:25]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 3028194LithiumHCID 12537863HCID 12537863, compoundHCID 178506676HCID 178506676, compound2×

Product 1

HCID 12519354HCID 12519354, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of phenyl lithium, which had been prepared by the reaction of 1.23 g. of lithium and 16.80 g. of bromobenzene, in 50 ml. of absolute ether was dropwise added a solution of 120 g. of 3-benzoylquinolizidine in absolute ether. The mixture was refluxed for 30 mins. with stirring. After the excess of phenyl lithium was decomposed with water, the reaction mixture was extracted with ether. The thus obtained etheral layer was washed with water and dried. After removing the solvent by distillation, α,α-diphenyl-quinolizidine-3-methanol showing a melting point of 166° to 167° C. was obtained.

Workup

  1. temperatureThe mixture was refluxed for 30 mins
  2. extractionthe reaction mixture was extracted with ether
  3. washThe thus obtained etheral layer was washed with water
  4. customdried
  5. customAfter removing the solvent
  6. distillationby distillation, α,α-diphenyl-quinolizidine-3-methanol showing a melting point of 166° to 167° C.
  7. customwas obtained

Sources & evidence

ORD record
ord-1f32664ed18c45ccb033c81857308d1b
Source dataset
uspto-grants-1980_05
Patent number
US04205074

Reaction notes

Loading…