Methyl iodide → HCID 71523276, compound

HRID 2358900Notes

Reaction equation

HRID 2358900 reaction equation
[CH3:1][C:2]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:3]=1[C:4]([O:6][CH:7]([CH3:17])[CH2:8][N:9]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:10])=[O:5].[CH3:24][I:25]>ClCCCl.C(Cl)Cl>[I-:25].[CH3:10][N+:9]([CH3:24])([CH2:8][CH:7]([O:6][C:4](=[O:5])[C:3]1[C:18]([CH3:23])=[CH:19][C:20]([CH3:22])=[CH:21][C:2]=1[CH3:1])[CH3:17])[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 86681543HCID 86681543, compound

Product 1

HCID 71523276HCID 71523276, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(cyclohexyl(methyl)amino)propan-2-yl 2,4,6-trimethylbenzoate (0.30 g, 0.946 mmol) in DCE (5 mL), methyl iodide (0.12 mL, 1.892 mmol) was added. The resultant reaction mixture was stirred at rt for 16 hours. The reaction mixture was diluted with DCM and concentrated to dryness. The crude product was subjected to column chromatography to obtain N,N-dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide. Yield: 0.109 g (25%). 1H NMR (400 MHz, CDCl3) δ 6.86 (s, 2 H), 5.70-5.67 (m, 1 H), 4.52-4.48 (d, J=14 Hz, 1 H), 3.83-3.77 (m, 1 H), 3.70-3.64 (m, 1 H), 3.34 (s, 3 H), 3.28 (s, 3 H), 2.29-2.01 (m, 10 H), 2.01-1.98 (m, 1 H), 1.84 (m, 1 H), 1.64-1.62 (d, J=6 Hz, 4 H), 1.47-1.38 (m, 4 H), 1.13-1.08 (m, 2 H). LCMS: m/z=332.2 [M+], RT=3.01 min (Column: Y, Program: P1). HPLC: 99.53% (200 nm), RT 4.11 min (Mobile phase: A: ACN, B: 0.05% TFA in water, Column: Zorbax® SBC18 (50*4.6 mm) 1.8μ.

Workup

  1. customThe resultant reaction mixture
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-429f6a358a1e4e669476dccc71a4e1de
Source dataset
uspto-grants-2014_04
Patent number
US08685418B2

Reaction notes

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