Dimethylamine → N-[2-[4-oxocyclohexyl]ethyl] 2-propanesulfonamide

HRID 566476Notes

Reaction equation

HRID 566476 reaction equation
C(CC1C=CC([C:11]2[CH2:16][CH2:15][CH:14]([CH:17](C)CCC(S(N)(=O)=O)C)[CH2:13][CH:12]=2)=CC=1)(O)=O.S(Cl)(Cl)=[O:28].C[NH:32][CH3:33].[S:34](=[O:38])(=O)(O)[O-:35].[Na+].O1C[CH2:43][CH2:42][CH2:41]1>ClCCl>[O:28]=[C:11]1[CH2:12][CH2:13][CH:14]([CH2:17][CH2:33][NH:32][S:34]([CH:42]([CH3:43])[CH3:41])(=[O:38])=[O:35])[CH2:15][CH2:16]1

Participants

7

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 516919Sodium BisulfateHCID 867562312-[4-(4-Carboxymethylphenyl)-3-cyclohexen-1-yl]propyl 2-propanesulfonamide

Product 1

HCID 22624691N-[2-[4-oxocyclohexyl]ethyl] 2-propanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1 equivalent of N-[2-[4-(4-carboxymethylphenyl)-3-cyclohexen-1-yl]propyl 2-propanesulfonamide (see Example 31) in tetrahydrofuran is treated with 10 eq. of thionyl chloride and stirred at room temperature for 16 hours. The mixture is then concentrate in vacuo, dissolved in dichloromethane and added to a 0° C. solution of 1 eq. of dimethylamine in dichloromethane. The mixture is stirred at 0° C. for 2 hours. and 10% aqueous sodium bisulfate is added. The organic layer is separated and the aqueous layer is extracted two times with dichloromethane. The combined organic extracts are dried over NaSO4, filtered and concentrate in vacuo to provide the crude material. Chromatography of the crude material affords the title compound.

Workup

  1. concentrationThe mixture is then concentrate in vacuo
  2. dissolutiondissolved in dichloromethane
  3. stirringThe mixture is stirred at 0° C. for 2 hours
  4. customThe organic layer is separated
  5. extractionthe aqueous layer is extracted two times with dichloromethane
  6. dry with materialThe combined organic extracts are dried over NaSO4
  7. filtrationfiltered
  8. concentrationconcentrate in vacuo
  9. customto provide the crude material

Sources & evidence

ORD record
ord-08b3e21c58dc48f085910346c298f3e0
Source dataset
uspto-grants-2001_01
Patent number
US06174922B1

Reaction notes

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