Methyl iodide → HCID 71522298, compound

HRID 709017Notes

Reaction equation

HRID 709017 reaction equation
[CH:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([O:10][CH:11]([CH3:21])[CH2:12][N:13]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH3:14])=[O:9])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:24][I:25]>ClCCCl>[I-:25].[CH:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([O:10][CH:11]([CH3:21])[CH2:12][N+:13]([CH3:24])([CH3:14])[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:9])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86681546HCID 86681546, compound

Product 1

HCID 71522298HCID 71522298, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-(cyclohexyl(methyl)amino)propan-2-yl 4-isopropylbenzoate (0.5 g, 1.57 mmol) in DCE (5 mL, methyl iodide (0.2 mL, 3.15 mmol) was added. The resultant reaction mixture was stirred at rt for 16 hours. The solvent was evaporated, and the crude product was purified by column chromatography. The product isolated was re-crystallized from methanol/ether. Yield: 134.9 mg (18.65%). 1H NMR (400 MHz, DMSO-d6) δ 7.94-7.92 (d, J=8 Hz, 2H), 7.43-7.41 (d, J=8 Hz, 2H), 5.54-5.50 (m, 1H), 3.95-3.89 (m, 1H), 3.61-3.58 (d, J=14 Hz, 1H), 3.40-3.34 (m, 1H), 3.03-2.95 (m, 7H), 2.22-2.20 (d, J=11 Hz, 1H), 2.10-2.07 (d, J=11 Hz, 1H), 1.86-1.83 (m, 2H), 1.57-1.43 (m, 3H), 1.36-1.35 (d, J=6 Hz, 3H), 1.16-1.11 (m, 9H). LCMS: m/z=331.8 [M+], RT=3.08 min (Column: Y, Program: P1). UPLC: 99.65% (200 nm), RT 3.09 min (Mobile phase: A. ACN, B. 0.05% HCOOH in water, Column: Gemini® NX C18 (50*4.6 mm) 3μ.

Workup

  1. customThe resultant reaction mixture
  2. customThe solvent was evaporated
  3. customthe crude product was purified by column chromatography
  4. customThe product isolated
  5. customwas re-crystallized from methanol/ether
  6. custom99.65% (200 nm), RT 3.09 min

Sources & evidence

ORD record
ord-07315f7b60304ec2b41b7d119418e027
Source dataset
uspto-grants-2015_11
Patent number
US09180115B2

Reaction notes

Loading…