4-Phenylpiperidin-4-ol → 4-(4-Hydroxy-4-phenylpiperidin-1-yl)naphthalene-1-carbonitrile

HRID 916330Notes

Reaction equation

HRID 916330 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](F)=[CH:5][CH:4]=1)#[N:2].[OH:14][C:15]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>N1C=CC=CC=1>[OH:14][C:15]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:20][CH2:19][N:18]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 963874-Phenylpiperidin-4-olHCID 27367341-Cyano-4-fluoronaphthalene

Product 1

HCID 692276844-(4-Hydroxy-4-phenylpiperidin-1-yl)naphthalene-1-carbonitrileYield 36.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

1-Cyano-4-fluoronaphthalene (20 mg, 0.117 mmol) was dissolved in pyridine (1 mL). 4-Hydroxy-4-phenylpiperidine (83 mg, 0.467 mmol) was added and the reaction mixture was shaken at 110° C. for 3 days in a sealed vial. The reaction mixture was concentrated and re-suspended in 2 M HCl (1 mL). The product mixture was extracted with ethyl acetate (2×1 mL), and the combined organic phases were concentrated. The residue was purified by preparative reversed phase HPLC to give the title compound (14 mg, 36% yield) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe product mixture was extracted with ethyl acetate (2×1 mL)
  3. concentrationthe combined organic phases were concentrated
  4. customThe residue was purified by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-f582e80f0fb6413ca4c4bf8ba17eb249
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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