Methyl iodide → 1-Cyclobutyl-4-[(1-ethyl-2-naphthalen-1-yl-1H-imidazol-4-yl)-methoxy-methyl]-piperidine

HRID 12474Notes

Reaction equation

HRID 12474 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([CH:11]([C:13]3[N:14]=[C:15]([C:20]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH:23]=[CH:22][CH:21]=4)[N:16]([CH2:18][CH3:19])[CH:17]=3)[OH:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:32]I>CN(C=O)C.CCOC(C)=O>[CH:1]1([N:5]2[CH2:6][CH2:7][CH:8]([CH:11]([C:13]3[N:14]=[C:15]([C:20]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH:23]=[CH:22][CH:21]=4)[N:16]([CH2:18][CH3:19])[CH:17]=3)[O:12][CH3:32])[CH2:9][CH2:10]2)[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59337851(1-cyclobutyl-piperidin-4-yl)-(1-ethyl-2-naphthalen-1-yl-1H-imidazol-4-yl)-methanol

Product 1

HCID 593381021-Cyclobutyl-4-[(1-ethyl-2-naphthalen-1-yl-1H-imidazol-4-yl)-methoxy-methyl]-piperidine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1-cyclobutyl-piperidin-4-yl)-(1-ethyl-2-naphthalen-1-yl-1H-imidazol-4-yl)-methanol (20 mg) in DMF (2 ml) is added NaH (6 mg, 60%), followed by CH3I (15 mg). The resulting mixture is stirred at rt for 30 min, and then diluted with EtOAc, washed with water and brine, dried and solvent removed. The crude product is purified by column (2% Et3N, 3% MeOH in EtOAc) to afford the title compound as an oil. LCMS 404.1 (M+1). 1H NMR (CDCl3) δ ppm 1.25 (t, 3H), 1.40-2.05 (m, 11H), 2.60 (m, 1H), 2.90 (m, 2H), 3.36 (s, 3H), 3.75 (q, 214), 4.05 (d, 1H), 7.02 (s, 1H), 7.42-7.60 (m, 5H), 7.86-7.96 (m, 2H).

Workup

  1. washwashed with water and brine
  2. customdried
  3. customsolvent removed
  4. customThe crude product is purified by column (2% Et3N, 3% MeOH in EtOAc)

Sources & evidence

ORD record
ord-996368e539504cb7806c1a8a3ac7055d
Source dataset
uspto-grants-2010_06
Patent number
US07728009B1

Reaction notes

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