Sodium Chloride → HCID 18919840, compound

HRID 1291123Notes

Reaction equation

HRID 1291123 reaction equation
[CH3:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[O:7])=[C:4]([NH:24]C(=O)C(F)(F)F)[CH:3]=1.O1CCOCC1.[Cl-].[Na+]>N1CCCCC1>[NH2:24][C:4]1[CH:3]=[C:2]([CH3:1])[CH:23]=[CH:22][C:5]=1[C:6]([O:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13][CH2:14]1)=[O:7]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 312751,4-DioxaneHCID 18919942HCID 18919942, compound

Product 1

HCID 18919840HCID 18919840, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

1.22 g (0.0029 mol) of 1-benzyl-piperidin-4-yl 4-methyl-2-trifluoroacetamido-benzoate were suspended in 60 ml of 1N aqueous piperidine in an ultrasound bath for 1/2 hr., treated with 10 ml of dioxan and subsequently stirred at room temperature for 20 hrs. Subsequently, the mixture was heated to 50° for 5 hrs. The suspension was treated with saturated aqueous sodium chloride solution and extracted with ethyl acetate. The organic phases were dried over sodium sulfate and concentrated and the residue was chromatographed on silica gel with ethyl acetate/hexane (1:2). 0.82 g (87%) of 1-benzyl-piperidin-4-yl 2-amino-4-methyl-benzoate was obtained as a colorless oil.

Workup

  1. temperatureSubsequently, the mixture was heated to 50° for 5 hrs
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phases were dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue was chromatographed on silica gel with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-7348935433ac40d1b0db3da9ef4bcdca
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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