Methyl iodide → HCID 67310535, compound

HRID 2061068Notes

Reaction equation

HRID 2061068 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([CH3:13])[CH3:12])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:25][I:26]>C(O)C>[I-:26].[C:1]([N:4]1[CH2:5][CH2:6][N+:7]([CH2:10][C:11]([NH:14][C:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:24])([CH3:13])[CH3:12])([CH3:25])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 60134557HCID 60134557, compound

Product 1

HCID 67310535HCID 67310535, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzyl 1-(4-acetylpiperazin-1-yl)-2-methylpropan-2-ylcarbamate (2.62 g, 7.86 mmol) was placed into a 15 mL pressure tube. Absolute ethanol (1.1 mL, 7.1 M) and methyl iodide (2.45 mL, 5 equiv, 39.3 mmol) was added to the pressure tube. A stir bar was added and the pressure tube sealed. The reaction was left to stir at room temperature for 7 days. The dark red solution was concentrated to a red oil which became a foam after drying under high vacuum. The foam was purified via Prep-LC using isocratic 95% water and 5% methanol for 5 min followed by a gradient to 95% methanol and 5% water over 16 min. Fraction were pooled to give recovered starting material (0.68 g, 20%) and product as a yellow foam (1.69 g, 45%). 1H NMR (D2O, 400 MHz): δ 1.51 (s, 6H), 2.12 (s, 3H), 3.23 (s, 3H), 3.35-3.60 (m, 5H), 3.68-3.85 (m, 4H), 3.92-4.02 (m, 1H), 5.11 (s, 2H), 7.38-7.48 (m, 5H). LRMS (ESI+) for C19H30N3O3+ (348.2); Found: 348 (M+).

Workup

  1. additionA stir bar was added
  2. customthe pressure tube sealed
  3. waitThe reaction was left
  4. concentrationThe dark red solution was concentrated to a red oil which
  5. customafter drying under high vacuum
  6. customThe foam was purified via Prep-LC
  7. customfor 5 min
  8. waitfollowed by a gradient to 95% methanol and 5% water over 16 min
  9. customto give
  10. customrecovered

Sources & evidence

ORD record
ord-5ffe07ae1a274bc680469666a718adbb
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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