Methyl iodide → HCID 86720921, compound

HRID 524863Notes

Reaction equation

HRID 524863 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH2:4][CH:3]1[CH2:17][OH:18].[H-].[Na+].[CH3:21]I>CN(C=O)C>[CH3:21][O:18][CH2:17][CH:3]1[CH2:4][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH2:6][CH2:7][N:2]1[CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86720922HCID 86720922, compound

Product 1

HCID 86720921HCID 86720921, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (1-methyl-4-(3-nitropyridin-4-yl)piperazin-2-yl)methanol (prepared according to methods similar to the one depicted in Step 1 of Preparation N-1) (250 mg, 0.9910 mmol) in DMF (2 mL) at 0° C. was added NaH (59.43 mg, 1.486 mmol). The reaction mixture was stirred for 10 min before MeI (281.3 mg, 123.40 μL, 1.982 mmol) was added dropwise. The reaction mixture was allowed to warm to RT and was stirred for 2 hours. The reaction mixture was loaded on a pre-washed SCX column, rinsed with MeOH and the product was released with methanolic ammonia. The ammonia extracts were concentrated under reduced pressure. The residue was purified by column chromatography on silica, eluting with 1-15% MeOH:DCM yielding 2-(methoxymethyl)-1-methyl-4-(3-nitropyridin-4-yl)piperazine (84 mg, 32%). MS (ES+) 237.1.

Workup

  1. additionwas added dropwise
  2. washrinsed with MeOH
  3. concentrationThe ammonia extracts were concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica
  5. washeluting with 1-15% MeOH

Sources & evidence

ORD record
ord-17ae51739f504601851731635684faa5
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

Loading…