2-Dimethylaminopyridine → HCID 18919942, compound

HRID 1291122Notes

Reaction equation

HRID 1291122 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH:3]=1.CN(C1C=CC=CN=1)C.[CH2:27]([N:34]1[CH2:39][CH2:38][CH:37](O)[CH2:36][CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH:37]2[CH2:36][CH2:35][N:34]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:39][CH2:38]2)=[O:7])=[C:4]([NH:11][C:12](=[O:17])[C:13]([F:14])([F:15])[F:16])[CH:3]=1

Participants

6

Reactant 4

HCID 218852-DimethylaminopyridineHCID 784611-Benzylpiperidin-4-olHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18919795HCID 18919795, compound

Product 1

HCID 18919942HCID 18919942, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.12 g (0.00453 mol) of 4-methyl-2-trifluoroaceta-mido-benzoic acid were dissolved in 23 ml of dimethylformamide, treated with 0.277 g (0.00227 mol) of dimethylaminopyridine and cooled to 00. 0.867 g (0.00453 mol) of 1-benzyl-4-hydroxy-piperidine and 0.955 g (0.005 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-sat. 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. 1.27 g (77%) of 1-benzyl-piperidin-4-yl 4-methyl-2-trifluoroacetamido-benzoate were obtained as a yellow oil. MS: me/e=421 (C22H24F3N2 O3 +).

Workup

  1. temperaturecooled to 00
  2. stirringThe mixture was stirred at room temperature for 48 hrs
  3. distillation, the solvent was distilled off
  4. washwashed with semi-sat
  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-9f69c2f7b9f84dc5a8c067b29b22d8c4
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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