Ammonium formate → 6-Methoxy-1-{4-[2-(piperidin-1-yl)ethoxy]phenoxy}naphthalen-2-ol

HRID 445199Notes

Reaction equation

HRID 445199 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]=1[O:21][C:22]1[CH:36]=[CH:35][C:25]([O:26][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:24][CH:23]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[OH-].[OH-].[Pd+2].CO.C(OCC)(=O)C>[CH3:20][O:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[C:10]([O:21][C:22]1[CH:23]=[CH:24][C:25]([O:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:35][CH:36]=1)=[C:9]([OH:8])[CH:18]=[CH:17]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 116774331-{2-[4-(2-Benzyloxy-6-methoxy-naphthalen-1-yloxy)-phenoxy]-ethyl}-piperidine

Product 1

HCID 583385476-Methoxy-1-{4-[2-(piperidin-1-yl)ethoxy]phenoxy}naphthalen-2-olYield 98.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

Add 1-{2-[4-(2-benzyloxy-6-methoxy-naphthalen-1-yloxy)-phenoxy]-ethyl}-piperidine (12.4 g, 25.5 mmol) to a methanol/ethyl acetate mixture (1:1, 490 mL) and heat to form a solution. Remove heat and add ammonium formate (4.83 g, 76.6 mmol) and Pd(OH)2 on Carbon (20% ww, 1.58 g, 1.12 mmol). Reflux the solution for 50 minutes then filter. Concentrate the filtrate to provide 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalene-2-ol (9.9 g, 25.1 mmol).

Workup

  1. temperatureheat
  2. customto form a solution
  3. customRemove
  4. temperatureheat
  5. temperatureReflux the solution for 50 minutes
  6. filtrationthen filter
  7. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-94a4e73243894106ac3c65969e1eedae
Source dataset
uspto-grants-2013_07
Patent number
US08476300B2

Reaction notes

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