Sodium Chloride → HCID 18919914, compound

HRID 1291120Notes

Reaction equation

HRID 1291120 reaction equation
[N+:1]([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])=[C:6]([NH:26]C(=O)C(F)(F)F)[CH:5]=1)([O-:3])=[O:2].[Cl-].[Na+]>N1CCCCC1>[NH2:26][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:25]=[CH:24][C:7]=1[C:8]([O:10][CH:11]1[CH2:12][CH2:13][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:16]1)=[O:9]

Participants

4

Reactant 2

HCID 5234Sodium ChlorideHCID 18919780HCID 18919780, compound

Product 1

HCID 18919914HCID 18919914, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

0.275 g (0.00061 mol) of 1-benzyl-piperidin-4-yl 4-nitro-2-trifluoroacetamido-benzoate was suspended in 12 ml of 1N aqueous piperidine in an ultrasound bath for 1/2 hr. and subsequently stirred at room temperature for 20 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, concentrated and chromatographed on silica gel with ethyl acetate/hexane (1:2). 0.20 g (92%) of 1-benzyl-piperidin-4-yl 2-amino-4-nitro-benzoate was obtained as a yellow oil. MS: me/e=356 (C19H22N3O4 +).

Workup

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

Sources & evidence

ORD record
ord-c89ca611e67b4d209bd36edd838496c5
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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