Methyl iodide → N-biphenyl-3-ylmethyl-N-methyl-acetamide

HRID 392831Notes

Reaction equation

HRID 392831 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9](=[O:11])[CH3:10])[CH:2]=1.[H-].[Na+].[CH3:20]I>C1(C)C=CC=CC=1>[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]([CH3:20])[C:9](=[O:11])[CH3:10])[CH:2]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22660935N-biphenyl-3-ylmethyl-acetamide

Product 1

HCID 22660885N-biphenyl-3-ylmethyl-N-methyl-acetamideYield 108%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-biphenyl-3-ylmethyl-acetamide (860 mg, 3.8 mmol) was dissolved in 10 mL of toluene. To this was added 611 mg of 60% NaH (mineral oil) and MeI (0.48 mL, 7.6 mmol). The resulting mixture was stirred overnight then filtered. The solvent was removed under vacuum to yield 980 mg (108% yield) of N-biphenyl-3-ylmethyl-N-methyl-acetamide. HRMS ((M+H) calcd for C16H18N): 240.1389; found: 240.1398. 1H NMR and 13C NMR show a mixture of rotamers at room temperature. 1H NMR (500 MHz, CDCl3) δ: 2.17 (s), 2.19 (s), 2.96 (s), 2.99 (s), 4.60 (s), 4.66 (s), 7.15-7.60 (overlapping m). 13C NMR (125 MHz, CDCl3) δ: 21.55, 21.91, 33.84, 35.61, 50.66, 54.33, 125.05, 125.16, 126.25, 126.55, 126.85, 127.00, 127.20, 127.23, 127.42, 127.65, 128.79, 128.90, 129.06, 129.45, 137.19, 137.95, 140.65, 140.95, 141.64, 142.12, 170.79, 171.08.

Workup

  1. filtrationthen filtered
  2. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-d47887682451428f98f06907de54279a
Source dataset
uspto-grants-2004_10
Patent number
US06803378B2

Reaction notes

Loading…