2-Dimethylaminopyridine → 1-Benzyl-piperidin-4-yl 2-dimethylamino-benzoate

HRID 1291106Notes

Reaction equation

HRID 1291106 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].CN(C1C=CC=CN=1)C.[CH2:22]([N:29]1[CH2:34][CH2:33][CH:32](O)[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH:32]1[CH2:31][CH2:30][N:29]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:34][CH2:33]1)=[O:6]

Participants

6

Reactant 4

HCID 218852-DimethylaminopyridineHCID 691182-(Dimethylamino)benzoic acidHCID 784611-Benzylpiperidin-4-olHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 189197761-Benzyl-piperidin-4-yl 2-dimethylamino-benzoateYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.33 g (0.002 mol) of 2-dimethylaminobenzoic acid was dissolved in 10 ml of dimethylformamide, treated with 0.122 g (0.001 mol) of dimethylaminopyridine and 0.383 g (0.002 mol) of 1-benzyl-4-hydroxypiperidine and cooled to 0°. 0.422 g (0.0022 mol) of N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride was added and the mixture was stirred at 0° for a further 2 hrs. Subsequently, the mixture was stirred at room temperature for 3 days, the solvent was distilled off and the residue was chromatographed on silica gel with ethyl acetate/hexane (1:2). 0.31 g (46%) of 1-benzyl-piperidin-4-yl 2-dimethylamino-benzoate was obtained as a colorless oil.

Workup

  1. temperaturecooled to 0°
  2. stirringSubsequently, the mixture was stirred at room temperature for 3 days
  3. distillationthe solvent was distilled off
  4. customthe residue was chromatographed on silica gel with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-79eaf0e3929f46ba9c6fd28300d0b724
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

Loading…