Phosphorus oxychloride → 3,4,5,6,7,8-Hexahydro-1-((4-methoxyphenyl)methyl)isoquinoline

HRID 443021Notes

Reaction equation

HRID 443021 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10](=O)[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:10]2[C:2]3[CH2:3][CH2:4][CH2:5][CH2:6][C:1]=3[CH2:7][CH2:8][N:9]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 703658N-(2-(1-Cyclohexen-1-yl)ethyl)-2-(4-methoxyphenyl)acetamide

Product 1

HCID 30165913,4,5,6,7,8-Hexahydro-1-((4-methoxyphenyl)methyl)isoquinolineYield 105.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

27.3 g (0.1 mol) of N-[2-(cyclohexen-1-yl)ethyl]-p-methoxyphenylacetamide and 91.4 g (0.596 mol) of phosphorus oxychloride in 230 ml of toluene were heated to 100° C. under argon for 30 min. The mixture was then evaporated in a rotary evaporator, and the residue (46 g) was washed twice with 70 ml of petroleum ether and then dissolved in 270 ml of dichloromethane. The solution was added to 270 ml of a 12% strength aqueous ammonia solution at 0° C. with vigorous stirring. The organic phase was washed with 90 ml of water, dried over sodium sulfate and evaporated, giving 27.0 g of a viscous yellow-brown oil, which was used immediately for the hydrogenation.

Workup

  1. customThe mixture was then evaporated in a rotary evaporator
  2. washthe residue (46 g) was washed twice with 70 ml of petroleum ether
  3. dissolutiondissolved in 270 ml of dichloromethane
  4. additionThe solution was added to 270 ml of a 12% strength aqueous ammonia solution at 0° C. with vigorous stirring
  5. washThe organic phase was washed with 90 ml of water
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-6cdbe75945004d7bbbf59372a5a1dc0f
Source dataset
uspto-grants-1999_04
Patent number
US05892044

Reaction notes

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