Hydrochloric Acid → HCID 53840445, compound

HRID 565700Notes

Reaction equation

HRID 565700 reaction equation
[NH2:1][C:2]1[C:3]([CH3:37])=[C:4]([CH3:36])[C:5]2[O:9][C:8]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([C:18]([NH:20][CH:21]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=O)[CH2:14][CH2:13]3)([CH3:10])[CH2:7][C:6]=2[C:34]=1[CH3:35].Cl>O1CCCC1>[NH2:1][C:2]1[C:3]([CH3:37])=[C:4]([CH3:36])[C:5]2[O:9][C:8]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([CH2:18][NH:20][CH:21]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:14][CH2:13]3)([CH3:10])[CH2:7][C:6]=2[C:34]=1[CH3:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22110990HCID 22110990, compound

Product 1

HCID 53840445HCID 53840445, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-[(5-amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl]-N-(diphenylmethyl)-4-piperidinecarboxamide (1.3 g) in tetrahydrofuran (20 mL) was added 17 mL of 1 M borane tetrahydrofuran complex solution in tetrahydrofuran with ice-cooling and the mixture was refluxed under nitrogen gas for 23 hours. After this reaction mixture was cooled with ice, 12 mL of 5N-hydrochloric acid was added dropwise and the mixture was concentrated under reduced pressure. The residue was neutralized with sodium hydrogen carbonate and extracted with 2 portions of ethyl acetate. The pooled organic layer was washed with water and saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethanol=10:1) to give 0.89 g of 1-[(5-amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl]-N-(diphenylmethyl)-4-piperidinemethylamine. Yield 68%. This product was dissolved in methanol and a stoichiometric excess of 10% HCl solution in methanol was added dropwise. The mixture was concentrated under reduced pressure to provide the title compound.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was refluxed under nitrogen gas for 23 hours
  3. additionwas added dropwise
  4. concentrationthe mixture was concentrated under reduced pressure
  5. extractionextracted with 2 portions of ethyl acetate
  6. washThe pooled organic layer was washed with water and saturated aqueous NaCl
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bc14dff53f934878886a67e21a2c2bce
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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