Hexane → 14446-29-8

HRID 484391Notes

Reaction equation

HRID 484391 reaction equation
[CH:1]([NH:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.CCCCCC>ClCCl>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:1]=[N:3][CH2:4][CH2:5]2

Participants

5

Reactant 3

HCID 8058HexaneHCID 24819Phosphorus pentachlorideHCID 13562936N-[2-(3-Methoxyphenyl)ethyl]formamide

Product 1

HCID 1001219614446-29-8Yield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 29.4 Kg of N-formyl-3-methoxyphenethylamine in 30 litres of dichloromethane was added over 90 minutes to a well-stirred slurry of 38.4 Kg of phosphorus pentachloride in 30 litres of dichloromethane. An exothermic reaction ensued, causing the solvent to reflux at 35°-38° C. After addition was complete, the reaction mixture was hydrolysed by the addition of a mixture of 90 Kg of ice and 30 litres of hexane. After cooling the aqueous layer was separated, made basic with 144 Kg of 45% potassium hydroxide and extracted twice with 50 Kg of dichloromethane. After drying the organic layer with sodium sulfate the solvent was removed under reduced pressure to give 23 Kg of 6-methoxy-3,4-dihydroisoquinoline as an oil.

Workup

  1. customAn exothermic reaction
  2. temperatureto reflux at 35°-38° C
  3. additionAfter addition
  4. temperatureAfter cooling the aqueous layer
  5. customwas separated
  6. extractionextracted twice with 50 Kg of dichloromethane
  7. dry with materialAfter drying the organic layer with sodium sulfate the solvent
  8. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-e0ea5fc509584806bf031f01dfd6b5de
Source dataset
uspto-grants-1993_07
Patent number
US05231181

Reaction notes

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