Hydrochloric Acid → HCID 67004190, compound

HRID 1513927Notes

Reaction equation

HRID 1513927 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=1)=[O:13])=[C:7]([C:29]1[C:34]([F:35])=[CH:33][C:32]([F:36])=[CH:31][C:30]=1[F:37])[CH:6]=[CH:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[ClH:44]>C1COCC1>[ClH:44].[OH:13][CH:12]([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:18][CH:19]=1)[C:8]1[C:7]([C:29]2[C:30]([F:37])=[CH:31][C:32]([F:36])=[CH:33][C:34]=2[F:35])=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([OH:1])=[CH:3]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 67004176[6-Hydroxy-2-(2,4,6-trifluoro-phenyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Product 1

HCID 67004190HCID 67004190, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve [6-hydroxy-2-(2,4,6-trifluoro-phenyl)-naphthalen 1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (728 mg, 1.4 mmol) in THF (85 mL) and cool to 0° C. Add 1M lithium aluminum hydride in THF (5.8 mL, 5.8 mmol) and bring to room temperature. Heat the reaction to reflux for 30 minutes. Cool reaction and pour onto ice/chloroform to form a suspension. Add 6N HCl dropwise to obtain a pH of 1. Extract with 20% isopropyl alcohol in chloroform. Wash organic layer with brine, dry, filter, and concentrate in vacuo to yield 730 mg (100%) of the title compound. HPLC Rt (0.01% heptafluorobutyric acid:1.0% isopropylalcohol:water is mobile phase A and 0.01% heptafluorobutyric acid:1.0% isopropylalcohol:acetonitrile is mobile phase B; gradient: 5 to 95% B, Purity@254 nm)=2.41 (100%); mass spectrum (ion spray): m/z=508.3 (M+H).

Workup

  1. custombring to room temperature
  2. temperatureHeat
  3. customthe reaction
  4. temperatureto reflux for 30 minutes
  5. temperatureCool
  6. customreaction
  7. additionpour onto ice/chloroform
  8. customto form a suspension
  9. customto obtain a pH of 1
  10. extractionExtract with 20% isopropyl alcohol in chloroform
  11. dry with materialWash organic layer with brine, dry
  12. filtrationfilter
  13. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-14bc0395cb8e4fc5bb7dac2dab6d65e5
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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