Methyl iodide → HCID 67310515, compound

HRID 2061053Notes

Reaction equation

HRID 2061053 reaction equation
[CH3:1][I:2].[CH3:3][C:4]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:5]>C(O)C>[I-:2].[CH2:17]([O:16][C:15]([NH:14][C:4]([CH3:3])([CH3:5])[CH2:6][CH2:7][N+:8]1([CH3:1])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 60134471HCID 60134471, compound

Product 1

HCID 67310515HCID 67310515, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 15 mL pressure tube, methyl iodide (2.0 mL, 5 equiv, 31.3 mmol) was added to a stirred solution of benzyl 2-methyl-4-(piperidin-1-yl)butan-2-ylcarbamate (1.91 g, 6.27 mmol) in ethanol (2.0 mL, 3.1 M). The pressure tube was sealed and the reaction was left to stir for 3 days. The yellow solution was poured into a round bottomed flask and the tube rinsed with ethanol. The reaction mixture was concentrated in vacuo to a syrup. Repeated addition and evaporation of isopropyl alcohol (3×10 mL) from the flask followed by acetonitrile (50 mL) gave a white solid. This solid was recrystallized from isopropyl alcohol. The crystals were filtered and rinsed with a small amount of cold isopropyl alcohol and dried under high vacuum to give white crystals, (2.51 g, 89.6%). 1H NMR (D2O, 400 MHz): δ 1.30 (s, 6H), 1.43-1.82 (m, 6H), 2.04-2.10 (m, 2H), 2.84 (s, 3H), 3.04-3.24 (m, 6H), 5.08 (s, 2H), 7.38-7.50 (m, 5H). LRMS (ESI+) for C19H31N2O2+ (319.2); Found: 319 (M+).

Workup

  1. customThe pressure tube was sealed
  2. waitthe reaction was left
  3. additionThe yellow solution was poured into a round bottomed flask
  4. washthe tube rinsed with ethanol
  5. concentrationThe reaction mixture was concentrated in vacuo to a syrup
  6. additionaddition and evaporation of isopropyl alcohol (3×10 mL) from the flask
  7. customgave a white solid
  8. customThis solid was recrystallized from isopropyl alcohol
  9. filtrationThe crystals were filtered
  10. washrinsed with a small amount of cold isopropyl alcohol
  11. customdried under high vacuum
  12. customto give white crystals, (2.51 g, 89.6%)

Sources & evidence

ORD record
ord-caf033fe4ffc4af3b5ef3dcce8b2d9a2
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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