Hydrochloric Acid → HCID 86592317, compound

HRID 1830835Notes

Reaction equation

HRID 1830835 reaction equation
[C:1]1([C@H:7]2[C@@H:12]([NH2:13])[CH2:11][CH2:10][CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])=[CH:20][C:17]=1[CH:18]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[ClH:53]>C(Cl)Cl.C(OCC)(=O)C.C(O)(=O)C>[ClH:53].[ClH:53].[C:1]1([C@H:7]2[C@@H:12]([NH:13][CH2:18][C:17]3[CH:20]=[C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:31])([F:32])[F:33])[CH:22]=[CH:23][C:16]=3[O:15][CH3:14])[CH2:11][CH2:10][CH2:9][NH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 9812908(2S,3S)-2-phenylpiperidin-3-amineHCID 22049660HCID 22049660, compound

Product 1

HCID 86592317HCID 86592317, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

In 10 ml of methylene chloride were suspended 176 mg of (±)-cis-2-phenylpiperidin-3-ylamine, 280 mg of 2-methoxy-5-(2-trifluoromethylphenyl)benzaldehyde, 424 mg of sodium triacetoxyborohydride and 0.2 ml of acetic acid. This reaction mixture was stirred at room temperature for 16 hours, a saturated aqueous sodium hydrogen carbonate solution was added to the mixture and the resulting mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The concentrated residue was purified by silica gel column chromatography (chloroform/methanol=10/1) to give a colorless oily product. This product was dissolved in ethyl acetate, and treated with an ethyl acetate solution of 4N hydrochloric acid. The precipitated white crystals were collected by filtration and washed with ethanol, and dried under reduced pressure to give 243 mg of [(±)-cis-2-phenylpiperidin-3-yl][2-methoxy-5-(2-trifluoromethylphenyl)benzyl]amine dihydrochloride.

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe concentrated residue was purified by silica gel column chromatography (chloroform/methanol=10/1)
  6. customto give a colorless oily product
  7. filtrationThe precipitated white crystals were collected by filtration
  8. washwashed with ethanol
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-304619208ebe47349928d79aba424114
Source dataset
uspto-grants-2006_06
Patent number
US07067535B2

Reaction notes

Loading…