Methyl iodide → HCID 44288936, compound

HRID 264683Notes

Reaction equation

HRID 264683 reaction equation
[H-].[Na+].[CH2:3]([C@H:10]1[CH2:15][C@H:14]([NH:16][CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12][N:11]1[C:28](=[O:37])[C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([Cl:36])[CH:30]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:38]I>COCCOC>[CH2:3]([C@@H:10]1[CH2:15][C@@H:14]([N:16]([CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][CH:19]=2)[CH3:38])[CH2:13][CH2:12][N:11]1[C:28](=[O:37])[C:29]1[CH:30]=[C:31]([Cl:36])[CH:32]=[C:33]([Cl:35])[CH:34]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67726981HCID 67726981, compound

Product 1

HCID 44288936HCID 44288936, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

13.4 mg (0.446 mmol) of an 80% strength suspension of sodium hydride in mineral oil (suspended in hexane and decanted) are added in one portion to a solution of 150 mg (0.297 mmol) of (2S*,4R*)-2-benzyl-1-(3,5-dichlorobenzoyl)-N-(4-quinolylmethyl)-4-piperidinamine in 2 ml of 1,2-dimethoxyethane at 0° C. After 10 minutes at 0° C., the mixture is left to stir at RT for 30 minutes, again cooled to 0° C., and 22 μl (0.357 mmol) of methyl iodide are added. The mixture is then stirred at RT for 96 hours. The solvent is stripped off in a rotary evaporator, and the residue is chromatographed on silica gel with toluene/ethyl acetate (1:1). The title compound ##STR78## is obtained (20 mg, 13%) as white foam. TLC:toluene/ethyl acetate (1:1) Rf =0.45; FD-MS:M+ =517, 519.

Workup

  1. customin mineral oil (suspended in hexane and decanted)
  2. waitthe mixture is left
  3. temperatureagain cooled to 0° C.
  4. stirringThe mixture is then stirred at RT for 96 hours
  5. customThe solvent is stripped off in a rotary evaporator
  6. customthe residue is chromatographed on silica gel with toluene/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-997f50a0ecaf44cbb0717d14e71beceb
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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