2-Dimethylaminopyridine → HCID 18919780, compound

HRID 1291119Notes

Reaction equation

HRID 1291119 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH:5]=1)([O-:3])=[O:2].CN(C1C=CC=CN=1)C.[CH2:29]([N:36]1[CH2:41][CH2:40][CH:39](O)[CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH:39]2[CH2:38][CH2:37][N:36]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:41][CH2:40]2)=[O:9])=[C:6]([NH:13][C:14](=[O:19])[C:15]([F:16])([F:17])[F:18])[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 218852-DimethylaminopyridineHCID 784611-Benzylpiperidin-4-olHCID 605646Benzoic acid, 4-nitro-2-[(trifluoroacetyl)amino]-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 18919780HCID 18919780, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.39 g (0.0014 mol) of 4-nitro-2-trifluoroacetamido-benzoic acid was dissolved in 7 ml of dimethylformamide, treated with 0.0855 g (0.0007 mol) of dimethylaminopyridine and cooled to 0°. 0.268 g (0.0014 mol) of 1-benzyl-4-hydroxy-piperidine and 0.295 g (0.00154 mol) of N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride were added and the mixture was stirred at 0° for 2 hrs. Thereafter, the mixture was warmed to room temperature. The mixture was stirred at room temperature for 48 hrs., the solvent was distilled off and the residue was taken up in ethyl acetate and washed with semi-saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and concentrated and the residue was chromatographed on silica gel with ethyl acetate/hexane (1:2) as the eluent. 0.28 g (44%) of 1-benzyl-piperidin-4-yl 4-nitro-2-trifluoroacetamido-benzoate was obtained as a yellow oil. MS: me/e=452 (C21H21F3N3O5 +).

Workup

  1. temperaturecooled to 0°
  2. stirringThe mixture was stirred at room temperature for 48 hrs
  3. distillation, the solvent was distilled off
  4. washwashed with semi-saturated sodium bicarbonate solution
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue was chromatographed on silica gel with ethyl acetate/hexane (1:2) as the eluent

Sources & evidence

ORD record
ord-48ed9cce066348119b0111fc776d1186
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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