Methyl iodide → HCID 71523276, compound

HRID 709011Notes

Reaction equation

HRID 709011 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, 2H), 5.70-5.67 (m, 1H), 4.52-4.48 (d, J=14 Hz, 1H), 3.83-3.77 (m, 1H), 3.70-3.64 (m, 1H), 3.34 (s, 3H), 3.28 (s, 3H), 2.29-2.01 (m, 10H), 2.01-1.98 (m, 1H), 1.84 (m, 1H), 1.64-1.62 (d, J=6 Hz, 4H), 1.47-1.38 (m, 4H), 1.13-1.08 (m, 2H). 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-411133679d404c6bba0f38fd1315869c
Source dataset
uspto-grants-2015_11
Patent number
US09180115B2

Reaction notes

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