Water → Ethyl-methyl-{3-[3-(4-methyl-piperidin-1-yl)-4-nitro-phenyl]-prop-2-ynyl}-amine

HRID 1508123Notes

Reaction equation

HRID 1508123 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([C:17]#[C:18][CH2:19]O)[CH:11]=[CH:12][C:13]=2[N+:14]([O-:16])=[O:15])[CH2:4][CH2:3]1.[CH2:21]([N:23](CC)[CH2:24]C)[CH3:22].CS(Cl)(=O)=O.O>C(Cl)Cl.C(NC)C>[CH2:21]([N:23]([CH3:24])[CH2:19][C:18]#[C:17][C:10]1[CH:11]=[CH:12][C:13]([N+:14]([O-:16])=[O:15])=[C:8]([N:5]2[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]2)[CH:9]=1)[CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58994550HCID 58994550, compound

Product 1

HCID 58994459Ethyl-methyl-{3-[3-(4-methyl-piperidin-1-yl)-4-nitro-phenyl]-prop-2-ynyl}-amineYield 100%

Reagents, catalysts & solvents 2

HCID 12219N-MethylethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-[3-(4-methyl-piperidin-1-yl)-4-nitro-phenyl]-prop-2-yn-1-ol (as prepared in the previous step, 47 mg, 0.17 mmol) in 4 mL of DCM at 0° C. was added triethylamine (71 μL, 0.51 mmol) followed by methanesulfonyl chloride (17 μL, 0.22 mmol). The reaction was allowed to stir for 10 min, at which time ethylmethylamine (4 drops) was added. The result was heated at reflux for 20 min. and then poured into water (20 mL). The aqueous layer was extracted with DCM (2×25 mL), the organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was purified by preparative TLC (10%-MeOH—CHCl3) to afford 59 mg (100%) of the title compound as an oil. Mass spectrum (ESI, m/z) Calcd for C18H25N3O2, 316.1 (M+H). found 316.2.

Workup

  1. additionwas added
  2. temperatureThe result was heated
  3. temperatureat reflux for 20 min.
  4. extractionThe aqueous layer was extracted with DCM (2×25 mL)
  5. dry with materialthe organic layers were dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative TLC (10%-MeOH—CHCl3)

Sources & evidence

ORD record
ord-78af86d6f57346f3a8327c41b12221dc
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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