Potassium Carbonate → HCID 13361845, compound

HRID 2413486Notes

Reaction equation

HRID 2413486 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][NH:9][CH2:8][CH2:7]2.CS(O[CH2:19][CH:20]1[CH2:24][O:23][C:22]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=2[Cl:38])([CH2:25][N:26]2[CH:30]=[CH:29][N:28]=[CH:27]2)[O:21]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:46][C:47]1[CH:52]=[CH:51][C:50]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[CH:49][CH:48]=1>CN(C)C=O>[Cl:38][C:32]1[CH:33]=[C:34]([Cl:37])[CH:35]=[CH:36][C:31]=1[C:22]1([CH2:25][N:26]2[CH:30]=[CH:29][N:28]=[CH:27]2)[O:21][CH:20]([CH2:19][O:3][C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH2:10][N:9]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([C:53]4[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=4)=[CH:49][CH:48]=2)[CH2:8][CH2:7]3)[CH2:24][O:23]1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 154634-Phenylbenzyl chlorideHCID 24758Sodium hydrideHCID 266981,2,3,4-Tetrahydroisoquinolin-6-olHCID 11177254HCID 11177254, compound

Product 1

HCID 13361845HCID 13361845, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

0.26 g of sodium hydride (50% suspension in oil) is added to a solution of 0.75 g of 6-hydroxy-1,2,3,4-tetrahydroisoquinoline in 30 ml of dimethylformamide, and the mixture is stirred at 50° C. for 30 minutes. Then 2.04 g of (2RS,4SR)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl methanesulfonate are introduced, and the mixture is stirred at 80° C. for 5 hours. It is allowed to cool, 1.00 g of finely powdered potassium carbonate and 1.00 g of 4-chloromethylbiphenyl are added, and the mixture is stirred at 60° C. for a further 5 hours. After cooling, the solvent is removed at the oil pump in a rotary evaporator, and the residue is taken up with a mixture of 50 ml of water and 50 ml of methylene chloride. The organic phase is washed twice more with water, dried over magnesium sulfate and evaporated in a rotary evaporator. To purify the crude product, it is chromatographed on silica gel using a mixture of ethyl acetate and methanol 19:1. 1.7 g of a viscous oil (57% of theory) which gradually crystallizes is obtained. Melting point 103°-105°.

Workup

  1. stirringthe mixture is stirred at 80° C. for 5 hours
  2. temperatureto cool
  3. stirringthe mixture is stirred at 60° C. for a further 5 hours
  4. temperatureAfter cooling
  5. customthe solvent is removed at the oil pump in a rotary evaporator
  6. additionthe residue is taken up with a mixture of 50 ml of water and 50 ml of methylene chloride
  7. washThe organic phase is washed twice more with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in a rotary evaporator
  10. customTo purify the crude product, it
  11. customis chromatographed on silica gel using
  12. additiona mixture of ethyl acetate and methanol 19:1
  13. custom1.7 g of a viscous oil (57% of theory) which gradually crystallizes
  14. customis obtained

Sources & evidence

ORD record
ord-63f78edcdbe847cc9299fd72f06ee487
Source dataset
uspto-grants-1988_01
Patent number
US04717724

Reaction notes

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