Hydrochloric Acid → HCID 16119324, compound

HRID 1433173Notes

Reaction equation

HRID 1433173 reaction equation
[CH3:1][CH:2]1[NH:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9](=O)[C@@H:10]([C:22]2([OH:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=2)[CH2:3]1.B.C1COCC1.Cl>C1COCC1>[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][C@@H:10]([C:22]2([OH:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 69076363HCID 69076363, compound

Product 1

HCID 16119324HCID 16119324, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solution of 1-(3,5-Dimethyl-piperazin-1-yl)-2-(R)-(1-hydroxy-cyclohexyl)-2-(3-trifluoromethoxy-phenyl)-ethanone (24.7 g, 59.6 mmol) in THF (140 mL) was added BH3.THF (300 mL, 1M, 300 mmol). The resultant mixture was heated to reflux for 22 h. On a smaller scale this reaction only takes about 2 h. After cooling down, 2N aqueous HCl (500 mL) was added to the mixture. After heating to reflux for 1 h, the mixture was allowed to cool down to RT and extracted with ethyl acetate (300 mL). The aqueous phase was basified with 50% NaOH to PH=12 and extracted with ethyl acetate (400 mL×4). The organic extracts were dried over Na2SO4 and concentrated in vacuo to provide crude 1-{(1S)-2-[cis-3,5-dimethylpiperazine-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl}-cyclohexanol (14.6 g, 61%).

Workup

  1. temperatureto reflux for 22 h
  2. customOn a smaller scale this reaction only takes about 2 h
  3. temperatureAfter cooling down
  4. temperatureAfter heating
  5. temperatureto reflux for 1 h
  6. extractionextracted with ethyl acetate (300 mL)
  7. extractionextracted with ethyl acetate (400 mL×4)
  8. dry with materialThe organic extracts were dried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7479bca49cca493dae550584774545c1
Source dataset
uspto-grants-2009_11
Patent number
US07612210B2

Reaction notes

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