N,N,N',N'-Tetramethylethylenediamine → HCID 18185379, compound

HRID 1358608Notes

Reaction equation

HRID 1358608 reaction equation
CC1(C)CCCC(C)(C)N1.C([Li])CCC.CN(C)CCN(C)C.[CH3:24][C:25]1([CH3:43])[CH2:29][O:28][C:27]([C:30]2[CH:31]=[CH:32][C:33]([N:36]3[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]3)=[N:34][CH:35]=2)=[N:26]1.CON(C)[C:47](=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CCCCCC>[CH3:24][C:25]1([CH3:43])[CH2:29][O:28][C:27]([C:30]2[C:31]([C:47]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:54])=[CH:32][C:33]([N:36]3[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH2:41]3)=[N:34][CH:35]=2)=[N:26]1

Participants

7

Reactant 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 130352,2,6,6-TetramethylpiperidineHCID 569575N-Methoxy-N-methylbenzamideHCID 18185391HCID 18185391, compoundHCID 178418339Butyllithium

Product 1

HCID 18185379HCID 18185379, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent3×

Conditions

Temperature
0 °C

Procedure

2,2,6,6-Tetramethylpiperidine (0.932 g, 6.6 mmol) was placed in a three-necked flask. Under argon 10 ml of hexane were added, the solution was cooled to 0° C. and n-butyl lithium (1.6 M solution in hexane) was added slowly. After stirring the yellow suspension for 10 min at 0° C., N,N,N′,N′-tetramethylethylenediamine (767 mg, 6.6 mmol) was added. This mixture was added dropwise to a suspension of 1.65 g (6 mmol) of 1-[5-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-pyridin-2-yl]-4-methyl-piperazine in 20 ml of hexane at −78°. After stirring the yellow solution for 30 min at this temperature and for 45 min at 0° C., a solution of 1.19 g N-methoxy-N-methyl benzamide (7.2 mmol) in 2 ml hexane/2 ml tetrahydrofuran was added slowly at 0° C. After 30 min, the cooling bath was removed and stirring was continued at room temperature overnight. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried (magnesium sulfate) and evaporated to give a brown oil, which was purified by flash chromatography with dichloromethane/methanol to yield 1.16 g (51%) of the product as a yellow solid.

Workup

  1. stirringAfter stirring the yellow solution for 30 min at this temperature
  2. waitfor 45 min at 0° C.
  3. waitAfter 30 min
  4. customthe cooling bath was removed
  5. stirringstirring
  6. waitwas continued at room temperature overnight
  7. additionWater was added
  8. extractionthe mixture was extracted with ethyl acetate
  9. dry with materialThe organic layer was dried (magnesium sulfate)
  10. customevaporated
  11. customto give a brown oil, which
  12. customwas purified by flash chromatography with dichloromethane/methanol

Sources & evidence

ORD record
ord-be04af758ea2452c8c6f975b0d74a84b
Source dataset
uspto-grants-2003_07
Patent number
US06596773B2

Reaction notes

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