Acetic Acid → 1-Methyl4-(4-prop-2-ynyl-phenyl)-piperazine

HRID 1984235Notes

Reaction equation

HRID 1984235 reaction equation
C(O)(=O)C.FC(F)(F)C(O)=O.[BH4-].[Na+].[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([CH:27](O)[C:28]#[CH:29])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1>C(Cl)Cl>[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][C:28]#[CH:29])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 577141411-[4-(4-Methyl-piperazin-1-yl)-phenyl]-prop-2-yn-1-ol

Product 1

HCID 577141261-Methyl4-(4-prop-2-ynyl-phenyl)-piperazineYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of glacial acetic acid (72 ml) and trifluoroacetic acid (8 ml), NaBH4 (79.1 mmol) is added slowly under nitrogen at −15° C. The solution of 1-[4-(4-methyl-piperazin-1-yl)-phenyl]-prop-2-yn-1-ol (1 1.3 mmol) in CH2Cl2 (80 ml) is added dropwise over 0.5 h and the mixture is stirred at room temperature for 1 h. The solvents are removed under reduced pressure and the residue is added to saturated sodium bicarbonate. The aqueous solution is extracted with CH2Cl2. The organic layer is washed with brine, dried over magnesium sulfate and evaporated down. The crude product is applied to silica gel column chromatography, which is eluted with following solvents: CH2Cl2 and 5% MeOH in CH2Cl2. The solvent of the latter effluent is removed by evaporation and dried in vacuo to afford the title compound. yield 86.8%, Rf=0.52 (CH2Cl2:MeOH=9:1).

Workup

  1. additionis added slowly under nitrogen at −15° C
  2. customThe solvents are removed under reduced pressure
  3. additionthe residue is added to saturated sodium bicarbonate
  4. extractionThe aqueous solution is extracted with CH2Cl2
  5. washThe organic layer is washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated down
  8. washis eluted with following solvents
  9. customThe solvent of the latter effluent is removed by evaporation
  10. customdried in vacuo

Sources & evidence

ORD record
ord-c429dc06342b4dc68ba2e173deb62d38
Source dataset
uspto-grants-2009_06
Patent number
US07544688B2

Reaction notes

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