Methanol → 4-[(2S,5R)-2,5-dimethylpiperazin-1-yl]-2-methoxybenzonitrile

HRID 1838254Notes

Reaction equation

HRID 1838254 reaction equation
C[C:2](C)([O-:4])C.[K+].CO.C1COCC1.[CH3:14][C@H:15]1[CH2:20][NH:19][C@H:18]([CH3:21])[CH2:17][N:16]1[C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24](F)[CH:23]=1>[Cl-].[Na+].O>[CH3:14][C@H:15]1[CH2:20][NH:19][C@H:18]([CH3:21])[CH2:17][N:16]1[C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([O:4][CH3:2])[CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 686909784-[(2S,5R)-2,5-Dimethylpiperazin-1-yl]-2-fluorobenzonitrile

Product 1

HCID 686912044-[(2S,5R)-2,5-dimethylpiperazin-1-yl]-2-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A 1.35 g portion of potassium tert-butoxide and 0.48 ml of methanol were added to 5 ml of THF, and the mixture was stirred for 30 minutes. Next, this was mixed with 934 mg of trans-4-(2,5-dimethylpiperazin-1-yl)-2-fluorobenzonitrile synthesized in Reference Example 14 and stirred at room temperature for 2 days. This was mixed with saturated brine and extracted with ethyl acetate, the organic layer was washed with water, and then the solvent was evaporated and the resulting mixture was subjected to a silica gel column chromatography and eluted with ethyl acetate-methanol-28% aqueous ammonia (9:1:0.1, v/v/v) to obtain 900 mg of the title compound.

Workup

  1. customsynthesized in Reference Example 14
  2. stirringstirred at room temperature for 2 days
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with water
  5. customthe solvent was evaporated
  6. washeluted with ethyl acetate-methanol-28% aqueous ammonia (9:1:0.1, v/v/v)

Sources & evidence

ORD record
ord-ecc0f26fc27e407d90e84573407eedb0
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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