N-Methylaniline → HCID 87551225, compound

HRID 1895974Notes

Reaction equation

HRID 1895974 reaction equation
C([O:8][C:9](Cl)(Cl)Cl)(OC(Cl)(Cl)Cl)=O.[CH3:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[C:29][CH:30]=[C:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[N:23]=1>C(Cl)Cl>[CH3:13][N:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]([N:34]1[CH2:35][CH2:36][C:31](=[CH:30][C:29]#[C:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([CH3:21])[N:23]=2)[CH2:32][CH2:33]1)=[O:8]

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 94429TriphosgeneHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 87551225HCID 87551225, compoundYield 242.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of ditrichloromethyl carbonate (43.6 mg, 0.147 mmol) in CH2Cl2 (1 mL) stirred at r.t., was added dropwise a solution of N-methylaniline (48.2 μL, 0.445 mmol) and DEA (168 μL, 0.98 mmol) in 1.5 mL of CH2Cl2 over 30′. After 40 min., was added a solution of the Compound of Example 3 (94.4 mg, 0.445 mmol) and 168 μL of DEA in 2 mL di CH2Cl2. After 24 h, the reaction mixture was evaporated to dryness in vacuo, taken up with water and extracted with EtOAc. The residue from extraction was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with Petroleum Ether-EtOAc gradient from 4:6 to 2:8 to afford the title compound (123 mg).

Workup

  1. waitAfter 24 h
  2. customthe reaction mixture was evaporated to dryness in vacuo
  3. extractionextracted with EtOAc
  4. extractionThe residue from extraction
  5. customwas purified by automated flash liquid chromatography (Horizon™-Biotage)
  6. washeluting with Petroleum Ether-EtOAc gradient from 4:6 to 2:8

Sources & evidence

ORD record
ord-7a9c6afb15854479a60f51ba3bd72ae4
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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