Piperidin-2-ylmethanol → 4-[2-(Hydroxymethyl)piperidin-1-yl]naphthalene-1-carbonitrile

HRID 916364Notes

Reaction equation

HRID 916364 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].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[CH2:20][OH:21]>N1C=CC=CC=1.C(OCC)(=O)C>[OH:21][CH2:20][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][N:14]1[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 94263Piperidin-2-ylmethanolHCID 27367341-Cyano-4-fluoronaphthalene

Product 1

HCID 687127624-[2-(Hydroxymethyl)piperidin-1-yl]naphthalene-1-carbonitrile

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-cyano-4-fluoronaphthalene (200 mg, 1.168 mmol) in pyridine (0.5 mL) was transferred to a Pyrex tube and 2-piperidinemethanol (538 mg, 4.67 mmol) was added. The tube was capped and exposed to microwave irradiation (200° C., 60 min). The reaction mixture was diluted with ethyl acetate, washed with 0.4 N HCl and saturated aqueous NaHCO3. The organic phase was dried and evaporated to give a crude product which was purified by preparative TLC (65:35 n-heptane/ethyl acetate), followed by further purification by preparative HPLC to give 173FBA70e (15 mg, 5%).

Workup

  1. additionwas added
  2. customThe tube was capped
  3. customexposed to microwave irradiation (200° C., 60 min)
  4. washwashed with 0.4 N HCl and saturated aqueous NaHCO3
  5. customThe organic phase was dried
  6. customevaporated

Sources & evidence

ORD record
ord-cc312c7f3d43444e980565bc5eb69a9f
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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