N-Methylbenzylamine → HCID 21181564, compound

HRID 1386520Notes

Reaction equation

HRID 1386520 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH:15]([CH3:17])[CH3:16])([CH2:11][CH2:12][CH2:13]Cl)[C:9]#[N:10].[CH3:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:27](=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH:15]([CH3:17])[CH3:16])([CH2:11][CH2:12][CH:13]([N:19]([CH3:18])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:27])[C:9]#[N:10]

Participants

6

Reactant 3

HCID 7669N-MethylbenzylamineHCID 11430Potassium CarbonateHCID 21181672HCID 21181672, compound

Product 1

HCID 21181564HCID 21181564, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of the product compound of Example 8, Step (b) (508 mg, 2.00 mmoles), methyl benzylamine (484 mg, 4.00 mmoles), and tetra-n-butylamrnonium iodide (74 mg) in dry dimethylformamide (2.0 mL) was added anhydrous potassium carbonate (552 mg, 4.00 imol). The mixture was stirred overnight at 80-85°. After cooling, the mixture was partitioned between diethyl ether and water, the aqueous layer was extracted with ether, the combined organic extracts were washed with brine, dried over sodium sulfate, filtered and the solvent evaporated. Chromatography of the residue over silica gel using 25% ethyl acetate-hexane as eluent gave a compound (540 mg) as an oil which was characterized by NMR, as follows: 1H NMR(CD2Cl2) d 7.63-6.95(m, 9H), 1.22(d, 3H), 0.82(d, 3H).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between diethyl ether and water
  3. extractionthe aqueous layer was extracted with ether
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-6f338d27eb294897bb6b07a5eabd742c
Source dataset
uspto-grants-2001_07
Patent number
US06265439B1

Reaction notes

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