Benzoic Acid → HCID 18919821, compound

HRID 1291177Notes

Reaction equation

HRID 1291177 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.CN(C1C=CC=CN=1)C.[C:26](O)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[C:26]([O:14][CH:11]1[CH2:10][CH2:9][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:16][CH:15]=2)[CH2:13][CH2:12]1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 100137731-[(4-Methoxyphenyl)methyl]-4-piperidinol

Product 1

HCID 18919821HCID 18919821, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.52 g (0.0023 mol) of 1-(4-methoxy-benzyl)-piperidin-4-ol was dissolved in 25 ml of dimethylformamide and treated with 0.14 g (0.0012 mol) of dimethylaminopyridine and 0.28 g (0.0023 mol) of benzoic acid. The mixture was cooled to 0° and 0.490 g (0.0025 mol) of N-ethyl-N'-(3-dimethylamino-propyl)-carbodiimide hydrochloride was added. The mixture was warmed to room temperature and stirred for 18 hrs. The solvent was distilled off and the residue was taken up in ethyl acetate and treated with silica gel. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane (1:3→1:2) as the eluent. 0.16 g (21%) of 1-(4-methoxy-benzyl)-piperidin-4-yl benzoate was obtained as a yellow oil. MS: me/e=326 (C20H24 NO3+).

Workup

  1. temperatureThe mixture was cooled to 0°
  2. distillationThe solvent was distilled off
  3. additiontreated with silica gel
  4. customAfter removal of the solvent the residue
  5. customwas chromatographed on silica gel with ethyl acetate/hexane (1:3→1:2) as the eluent

Sources & evidence

ORD record
ord-989dbadc32bf4c7cad77477a09df648b
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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