Methyl iodide → HCID 45378142, compound

HRID 38114Notes

Reaction equation

HRID 38114 reaction equation
[CH:1]1([NH:4][C:5](=[O:17])[CH2:6][NH:7][C@@H:8]2[CH2:10][C@H:9]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3][CH2:2]1.[CH3:18]I>C(#N)C>[CH:1]1([NH:4][C:5](=[O:17])[CH2:6][N:7]([CH3:18])[C@@H:8]2[CH2:10][C@H:9]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 45377984HCID 45377984, compound

Product 1

HCID 45378142HCID 45378142, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-cyclopropyl-N-methyl-trans-2-(phenylcyclopropyl amino)acetamide (example 1, 240 mg, 1 mmol) in acetonitrile (10 mL), methyl iodide (140 mg, 1 mmol) was added and the solution was refluxed for 1 h. The mixture was then concentrated in vacuo and the residue was purified by flash column chromatography (DCM:MeOH, 10:1) to afford the title compound as a white solid (200 mg, 57%). 1HNMR (CDCl3) δ (ppm): 0.44 (s, 2H), 0.73 (dd, 2H), 0.93 (m, 1H), 1.02 (m, 1H), 1.89 (m, 1H), 2.04 (m, 1H), 2.29 (s, 3H), 2.67 (m, 1H), 3.13 (m, 2H), 6.84 (br, 1H), 6.98 (d, 2H), 7.11 (q, 1H), 7.14 (m, 2H), 7.18 (d, 2H). MS (M+H): 244.7.

Workup

  1. temperaturethe solution was refluxed for 1 h
  2. concentrationThe mixture was then concentrated in vacuo
  3. customthe residue was purified by flash column chromatography (DCM:MeOH, 10:1)

Sources & evidence

ORD record
ord-1effdc935f1a498f8e7fa49f72b5ec7d
Source dataset
uspto-grants-2013_09
Patent number
US08524717B2

Reaction notes

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