Hydrochloric Acid → 1-{Hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-methoxy-naphthalen-2-ol

HRID 1513910Notes

Reaction equation

HRID 1513910 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]=1[C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:18][CH:17]=1)=[O:15].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1.O>[OH:15][CH:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)=[CH:18][CH:17]=1)[C:3]1[C:4]2[C:9](=[CH:8][C:7]([O:12][CH3:13])=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[OH:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 219316286-Methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-ol

Product 1

HCID 670047201-{Hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-methoxy-naphthalen-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (2-hydroxy-6-methoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (12 g, 29.6 mmol) in tetrahydrofuran (200 Add lithium aluminum hydride (3.0 g, 78.0 mmol) and heat the reaction to reflux. Allow to cool to room temperature and add ice. Adjust the pH of the mixture to 7 with 5 M hydrochloric acid. Dilute with water (500 mL). Wash the mixture four times with dichloromethane (500 mL each wash). Combine the organics, dry over sodium sulfate, decant, and concentrate in vacuo to give 1-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-methoxy-naphthalen-2-ol.

Workup

  1. temperatureheat
  2. customthe reaction
  3. temperatureto reflux
  4. additionadd ice
  5. washWash the mixture four times with dichloromethane (500 mL each wash)
  6. dry with materialCombine the organics, dry over sodium sulfate
  7. customdecant
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-62c15a62cbc947ae8a77068a8bb64e11
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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