Sodium Carbonate → HCID 18919737, compound

HRID 1291105Notes

Reaction equation

HRID 1291105 reaction equation
[CH:1]([NH:3][C:4]1[CH:25]=[CH:24][C:7]([C:8]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)=[O:9])=[CH:6][CH:5]=1)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[CH3:1][NH:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:13][CH2:12]2)=[O:9])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 18919755HCID 18919755, compound

Product 1

HCID 18919737HCID 18919737, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.338 g (0.001 mol) of 1-benzyl-piperidin-4-yl 4-formamido-benzoate was dissolved in 10 ml of THF, treated with 4.5 ml (0.0045 mol) of 1M BH3 -THF solution and boiled at reflux for 18 hrs. The reaction mixture was treated with 9 ml of 1N aqueous HCI and stirred at room temperature for 1 hr. The mixture was made basic with sat. sodium carbonate solution, extracted with ethyl acetate and the organic phase was subsequently extracted with sat. sodium chloride solution. It was dried over sodium sulfate and concentrated and the residue was chromatographed over silica gel with ethyl acetate/toluene (1:2). 0.105 g (32%) of 1-benzyl-piperidin-4-yl 4-methylamino-benzoate was obtained as a colorless oil.

Workup

  1. temperatureat reflux for 18 hrs
  2. additionThe reaction mixture was treated with 9 ml of 1N aqueous HCI
  3. extractionextracted with ethyl acetate
  4. extractionthe organic phase was subsequently extracted with sat. sodium chloride solution
  5. dry with materialIt was dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue was chromatographed over silica gel with ethyl acetate/toluene (1:2)

Sources & evidence

ORD record
ord-2232e8d39d2b4daab7f4aee3e76bf9d5
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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