Benzoic Acid → HCID 67330689, compound

HRID 1942557Notes

Reaction equation

HRID 1942557 reaction equation
[CH2:1]([NH:3][C@@H:4]1[C@@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=2)[CH2:8][CH2:7][N:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:5]1)[CH3:2].Cl.CN(C)CCCN=C=NCC.[C:36](O)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[Cl-].[NH4+]>C(Cl)Cl.C(N(CC)CC)C>[C:36]([O:16][C:12]1[CH:11]=[C:10]([C@H:9]2[CH2:8][CH2:7][N:6]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:5][C@@H:4]2[NH:3][CH2:1][CH3:2])[CH:15]=[CH:14][CH:13]=1)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67330916HCID 67330916, compound

Product 1

HCID 67330689HCID 67330689, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of tert-butyl (rac.)-(3R,4R)-3-(ethylamino)-4-(3-hydroxyphenyl)piperidine-1-carboxylate (1.76 g) in methylene chloride (16 ml) were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.37 g), N,N-dimethylaminopyridine (872 mg), triethylamine (995 μl), and benzoic acid (610 mg), and the mixture was stirred at room temperature for one hour. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous ammonium chloride solution, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (the developing solvent: hexane/ethyl acetate=1/1) to give the title compound (968 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous ammonium chloride solution
  3. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-3932d3c2e4954708bebd7192254f1986
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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