Ethanol → HCID 20269133, compound

HRID 485828Notes

Reaction equation

HRID 485828 reaction equation
Cl.[C:2]1([CH:8]2[C:17]3[C:12](=[C:13](Cl)[CH:14]=[CH:15][CH:16]=3)[CH:11]([NH:19][C:20](=[O:22])[CH3:21])[N:10]([CH3:23])[CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(O)(=O)/C=C\C(O)=O>CO>[C:2]1([CH:8]2[C:17]3[C:12](=[C:13]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[CH:14]=[CH:15][CH:16]=3)[CH:11]([NH:19][C:20](=[O:22])[CH3:21])[N:10]([CH3:23])[CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8083MorpholineHCID 444266Maleic AcidHCID 70490882HCID 70490882, compound

Product 1

HCID 20269133HCID 20269133, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7 g (0.02 mole) of 4-phenyl-8-chloro-acetylamino-2-methyl-1,2,3,4-tetrahydro-isoquinoline-hydrochloride, 70 ml of ethanol and 20 ml (20.0 g, 0.23 mole) of morpholine is refluxed for 5 hours. The reaction mixture is evaporated in vacuo, the residue is dissolved in a mixture of 200 ml of water and 200 ml of ether, 30 ml of a 30% aqueous sodium hydroxide solution is added, the layers are separated and the aqueous phase is extracted four times with 200 ml of ether each. The united ether solutions are dried over anhydrous sodium sulfate and evaporated. The oily residue (6.7 g) is dissolved in 100 ml of ethanol and a solution of 6.6 g (0.057 mole) of maleic acid and 30 ml of methanol is added. The precipitated product is filtered in the cold. The beige coloured dimaleate (10.7 g) is dissolved in 100 ml of water, the solution is made alkaline by adding 60 ml of a 35% aqueous sodium hydroxide solution and extracted once with 200 ml and four times with 100 ml of ether each. The ether phases are united, dried over anhydrous sodium sulfate, clarified with activated charcoal and dried. The ether is evaporated and the residue is crystallized from a mixture of ether and petrolether. Thus 5.1 g of (0.014 mole) of white crystalline 4-phenyl-2-methyl-8-morpholino-acetylamino-1,2,3,4-tetrahydro-isoquinoline are obtained. Mp.: 120° C.

Workup

  1. temperatureis refluxed for 5 hours
  2. customThe reaction mixture is evaporated in vacuo
  3. dissolutionthe residue is dissolved in a mixture of 200 ml of water and 200 ml of ether, 30 ml of a 30% aqueous sodium hydroxide solution
  4. additionis added
  5. customthe layers are separated
  6. extractionthe aqueous phase is extracted four times with 200 ml of ether each
  7. dry with materialThe united ether solutions are dried over anhydrous sodium sulfate
  8. customevaporated
  9. dissolutionThe oily residue (6.7 g) is dissolved in 100 ml of ethanol
  10. filtrationThe precipitated product is filtered in the cold
  11. dissolutionThe beige coloured dimaleate (10.7 g) is dissolved in 100 ml of water
  12. additionby adding 60 ml of a 35% aqueous sodium hydroxide solution
  13. extractionextracted once with 200 ml and four times with 100 ml of ether each
  14. dry with materialdried over anhydrous sodium sulfate
  15. customdried
  16. customThe ether is evaporated
  17. customthe residue is crystallized from a mixture of ether and petrolether

Sources & evidence

ORD record
ord-a7c13edc84964d36893f63d5e6345bdf
Source dataset
uspto-grants-1985_08
Patent number
US04537895

Reaction notes

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