Methyl iodide → HCID 67319186, compound

HRID 2061082Notes

Reaction equation

HRID 2061082 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH3:12])[CH3:11])[CH2:4][CH2:3]1.[CH3:25][I:26]>C(O)C>[I-:26].[CH2:16]([O:15][C:14]([NH:13][C:10]([CH3:11])([CH3:12])[CH2:9][CH2:8][N+:5]1([CH3:25])[CH2:6][CH2:7][C:2]([CH3:24])([CH3:1])[CH2:3][CH2:4]1)=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 60134584HCID 60134584, compound

Product 1

HCID 67319186HCID 67319186, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Benzyl 4-(4,4-dimethylpiperidin-1-yl)-2-methylbutan-2-ylcarbamate (2.25 g, 6.76 mmol) was placed into a 15 mL pressure tube. Absolute ethanol (2 mL) and Methyl iodide (5.0 mL, 11.8 equiv, 80.1 mmol) was added in one portion. A stir bar was added and the pressure tube sealed. The reaction was left to stir at 50° C. for 16 h. The solution was concentrated to a pale yellow solid. The crude solid was dissolved into isopropanol (5 mL) and ethyl acetate (25 mL) and the solution cooled in an ice bath to give a gel. The product was filtered, washed with fresh ethyl acetate and dried under high vacuum to give a white solid (2.06 g, 64.0%). 1H NMR (D2O, 400 MHz): δ 0.98 (s, 3H), 1.03 (s, 3H), 1.30 (s, 6H), 1.50-1.70 (m, 4 H), 2.10-2.18 (m, 2H), 2.85 (s, 3H), 3.15-3.28 (m, 6 H), 5.09 (s, 2H), 7.38-7.50 (m, 5H). LRMS (ESI+) for C21H35N2O2+ (347.3); Found: 347 (M+).

Workup

  1. additionA stir bar was added
  2. customthe pressure tube sealed
  3. waitThe reaction was left
  4. concentrationThe solution was concentrated to a pale yellow solid
  5. dissolutionThe crude solid was dissolved into isopropanol (5 mL) and ethyl acetate (25 mL)
  6. temperaturethe solution cooled in an ice bath
  7. customto give a gel
  8. filtrationThe product was filtered
  9. washwashed with fresh ethyl acetate
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-82a7fcf1d81e47fa8d11f8c5413989de
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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