Triethylamine → HCID 21993833, compound

HRID 1978329Notes

Reaction equation

HRID 1978329 reaction equation
O[CH2:2][C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].C([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])C.CS(Cl)(=O)=O.C(=O)([O-])O.[Na+]>O1CCCC1>[C:3]1([CH:2]2[CH2:25][CH2:24][N:23]([CH2:2][C:3]3[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=3[CH2:5][N:6]3[C:7](=[O:16])[C:8]4=[CH:15][CH:14]=[CH:13][CH:12]=[C:9]4[C:10]3=[O:11])[CH2:26][CH2:27]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 21994184HCID 21994184, compound

Product 1

HCID 21993833HCID 21993833, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2.704 g (10.117 mM) of N-[2-(hydroxymethyl)benzyl]phthalimide and 1.69 ml (12.1 mM) of triethylamine in 50 ml of tetrahydrofuran was added 0.86 ml (11.1 mM) of methanesulfonyl chloride dropwise with ice-cooling and the mixture was stirred at 0° C. for 0.5 hour. This reaction mixture was poured in aqueous solution of sodium hydrogen carbonate and extracted with 3 portions of ethyl acetate. The organic layers were combined and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was dissolved in 50 ml of N,N-dimethylformamide, followed by addition of 1.79 g (11.1 mM) of 4-phenylpiperidine and 2.80 g (20.2 mM) of potassium carbonate, and the mixture was stirred at 100° C. overnight. This reaction mixture was poured in water and extracted with 2 portions of ethyl acetate. The organic layers were combined and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1) to provide the title compound.

Workup

  1. temperaturecooling
  2. extractionextracted with 3 portions of ethyl acetate
  3. dry with materialdried over MgSO4
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionThe residue was dissolved in 50 ml of N,N-dimethylformamide
  6. additionfollowed by addition of 1.79 g (11.1 mM) of 4-phenylpiperidine and 2.80 g (20.2 mM) of potassium carbonate
  7. stirringthe mixture was stirred at 100° C. overnight
  8. additionThis reaction mixture was poured in water
  9. extractionextracted with 2 portions of ethyl acetate
  10. dry with materialdried over MgSO4
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1)

Sources & evidence

ORD record
ord-1e4984b9b58347789c3d92722eea74e9
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

Loading…