Hydrochloric Acid → 5-aminomethyl-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one bis-hydrochloride

HRID 496413Notes

Reaction equation

HRID 496413 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C:14](=[O:19])[C:13]=2[CH:12]=[CH:11][C:10]=1[O:20][C@@H:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:22][N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)(C)(C)C.[ClH:35]>O1CCOCC1>[ClH:35].[ClH:35].[NH2:7][CH2:8][C:9]1[C:10]([O:20][C@@H:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:22][N:23]2[CH:27]=[CH:26][N:25]=[CH:24]2)=[CH:11][CH:12]=[C:13]2[C:18]=1[CH2:17][CH2:16][CH2:15][C:14]2=[O:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60029890[2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 208287285-aminomethyl-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one bis-hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

[2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl]-carbamic acid tert-butyl ester (0.830 g, 1.80 mmol) was dissolved in dioxane (10 mL) and 4M HCl in dioxane (4 mL) was added. After 15 minutes, a white precipitate formed. The precipitate was collected by filtration, washed with Et2O and dried in a vacuum oven to give the title compound as a white fluffy solid (0.761 g, 1.75 mmol, 97%). The structure was confirmed by NMR, mass spectrometry and elemental analysis. MS m/z 362 (M++H).

Workup

  1. customa white precipitate formed
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with Et2O
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-ccca1b05e02b4f12adf6cf3b0d90045e
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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