Potassium Carbonate → HCID 68502118, compound

HRID 1176608Notes

Reaction equation

HRID 1176608 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([CH2:16][O:17][CH:18]3[CH:23]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32]OS(C5C=CC(C)=CC=5)(=O)=O)=[CH:26][CH:25]=4)[CH2:22][CH2:21][N:20]([C:44]([O:46][CH2:47][C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)=[O:45])[CH2:19]3)[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][C:7]1=O.Cl.[C:56]1([CH:62]2[CH2:66][CH2:65][NH:64][CH2:63]2)[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([CH2:16][O:17][CH:18]3[CH:23]([C:24]4[CH:25]=[CH:26][C:27]([O:30][CH2:31][CH2:32][N:64]5[CH2:65][CH2:66][CH:62]([C:56]6[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=6)[CH2:63]5)=[CH:28][CH:29]=4)[CH2:22][CH2:21][N:20]([C:44]([O:46][CH2:47][C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)=[O:45])[CH2:19]3)[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 441188043-Phenylpyrrolidine--hydrogen chloride (1/1)HCID 86610024HCID 86610024, compound

Product 1

HCID 68502118HCID 68502118, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.350 g of benzyl 3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-{4-[2-(toluene-4-sulphonyloxy)ethoxy]phenyl}piperidinecarboxylate (Example 267c) in 5 ml of N,N-dimethylformamide is admixed with 0.112 g of 3-phenylpyrrolidine hydrochloride, 0.199 g of potassium carbonate and 0.018 g of tetrabutylammonium iodide. The reaction mixture is subsequently stirred at 80° over 2 hours. The reaction mixture is cooled and poured onto 10 ml of saturated aqueous sodium hydrogencarbonate solution and extracted with tert-butyl methyl ether (2×20 ml). The organic phase is washed with 20 ml of brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F). Rf=0.26 (95:5 dichloromethane-methanol); Rt=5.03.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with tert-butyl methyl ether (2×20 ml)
  3. washThe organic phase is washed with 20 ml of brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-36b4746da8084067a6c6ef60e803fab7
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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