Water → HCID 2843106, compound

HRID 1500173Notes

Reaction equation

HRID 1500173 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.[CH3:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21].O>ClCCl>[CH3:1][CH:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][N:4]([C:20](=[O:21])[C:19]2[CH:23]=[CH:24][CH:25]=[C:17]([CH3:16])[CH:18]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 743753-Methylbenzoyl chlorideHCID 1182593,5-Dimethylpiperidine

Product 1

HCID 2843106HCID 2843106, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3,5-Dimethylpiperidine (0.73 g) and triethylamine (2.25 ml) were dissolved in dichloromethane (20 ml). A solution of 3-methylbenzoylchloride (1.00 g) in dichloromethane (10 ml) was added dropwise at the freezing point. After stirring for 30 minutes at 0° C., the reaction solution was poured into water (100 ml) and extracted with chloroform (50 ml). The organic layer was washed with saturated brine (100 ml), dried over anhydrous sodium sulfate and, after filtration, concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (developing solvent: n-hexane/ethyl acetate=4:1) to obtain the subject compound (NCR-1 cis form:trans form=9:1) (0.95 g, yield 63%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz, δ; ppm) 0.76-1.86 (10H, m), 2.15-2.23 (0.9H, m), 2.36 (3H, s), 2.44-2.49 (0.9H, m), 3.08 (0.1H, m), 3.20 (0.1H, m), 3.32-3.34 (0.1H, m), 3.63-3.65 (0.9H, m), 7.14 (1H, d, J=7.3 Hz), 7.19 (1H, d, J=7.3 Hz), 7.20 (1H, s), 7.26 (1H, t, J=7.6 Hz); MS (EI) m/z: 231 (M+).

Workup

  1. extractionextracted with chloroform (50 ml)
  2. washThe organic layer was washed with saturated brine (100 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationafter filtration
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash column chromatography (developing solvent: n-hexane/ethyl acetate=4:1)
  7. customto obtain
  8. customthe subject compound (NCR-1 cis form:trans form=9:1) (0.95 g, yield 63%) as a colorless oil

Sources & evidence

ORD record
ord-d0d1675f5ea7445fa1e3d9d8e4006e9f
Source dataset
uspto-grants-2015_12
Patent number
US09206125B2

Reaction notes

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