Methyl iodide → HCID 19919335, compound

HRID 1648326Notes

Reaction equation

HRID 1648326 reaction equation
[CH:1]([Li])(CC)C.CCCCCC.[CH2:12]([N:15]([CH2:33][CH2:34][CH3:35])[C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH2:18][CH2:19][CH2:20][N:21]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:13][CH3:14].CI>C1COCC1>[CH3:1][C:23]1[CH:24]=[CH:25][C:16]([N:15]([CH2:12][CH2:13][CH3:14])[CH2:33][CH2:34][CH3:35])=[C:17]2[C:22]=1[N:21]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:20][CH2:19][CH2:18]2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 19919287HCID 19919287, compoundHCID 178418400CID 53628100

Product 1

HCID 19919335HCID 19919335, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

s-Butyl lithium (17.7 mL of 1.3 M in hexane (0.045 mol) was added at -78° C. to a stirred solution of t-butyl 1,2,3,4-tetrahydro-5-(dipropylamino)quinoline-1-carboxylate (10 g, 0.030 mol) in THF (200 mL). After 15 minutes, methyl iodide (17.1 g, 0.13 mol) was added and the solution was allowed to warm to room temperature. The THF was removed under reduced pressure, and the residual oil was partitioned between ethyl acetate and water. The ethyl acetate was evaporated and the residual oil was chromatographed on silica gel to afford 10.65 g of t-butyl 1,2,3,4-tetrahydro-8-methyl-5-(dipropylamino)quinoline-1-carboxylate as an oil.

Workup

  1. customThe THF was removed under reduced pressure
  2. customthe residual oil was partitioned between ethyl acetate and water
  3. customThe ethyl acetate was evaporated
  4. customthe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-bac09fb69e744df8b2025e7e575ea512
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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