Sodium Chloride → HCID 18919739, compound

HRID 1291113Notes

Reaction equation

HRID 1291113 reaction equation
[F: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.[Cl-].[Na+]>N1CCCCC1>[NH2:24][C:4]1[CH:3]=[C:2]([F:1])[CH:23]=[CH:22][C:5]=1[C:6]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:7]

Participants

4

Reactant 2

HCID 5234Sodium ChlorideHCID 18919820HCID 18919820, compound

Product 1

HCID 18919739HCID 18919739, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

1.145 g (0.0027 mol) of 1-benzyl-piperidin-4-yl 4-fluoro-2-trifluoroacetamido-benzoate were suspended in 25 ml of 1N aqueous piperidine in an ultrasound bath for 1/2 hr. and subsequently stirred at room temperature for 48 hrs. The suspension was treated with semi-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 (1:3). 0.82 g (92%) of 1-benzyl-piperidin-4-yl 2-amino-4-fluoro-benzoate was obtained as a colorless oil. MS:=329 (C19H22FN2O2 +).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phases were dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue was chromatographed on silica gel with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-efeaad5c26dc45a29f05082895b9b304
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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