Trifluoroacetic acid → 2-Methyl-1-(piperazin-1-yl)propan-2-ol

HRID 1400955Notes

Reaction equation

HRID 1400955 reaction equation
[OH:1][C:2]([CH3:18])([CH3:17])[CH2:3][N:4]1[CH2:9][CH2:8][N:7](C(OCCCC)=O)[CH2:6][CH2:5]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:18][C:2]([OH:1])([CH3:17])[CH2:3][N:4]1[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86658604Butyl 4-(2-hydroxy-2-methylpropyl)piperazine-1-carboxylate

Product 1

HCID 2582022-Methyl-1-(piperazin-1-yl)propan-2-olYield 60.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 563 (460 mg, 1.78 mmol) and TFA (5 ml) in DCM (20 ml) was stirred at rt for 5 h. The reaction mixture was concentrated (azeotropes with DCM), diluted with water, stirred for 10 min. The pH was adjusted to around 10 with 1N NaOH, and the alkaline solution was extracted with DCM. The organic extract was dried over anhydrous magnesium sulfate, filtered, concentrated under high vacuum to afford the desired product 564 (170 mg, 1.07 mmol, 60% yield) as a dark orange sticky solid. The crude product was used in the next step without any further purification. MS (m/z): 159.13 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated (azeotropes with DCM)
  2. additiondiluted with water
  3. extractionthe alkaline solution was extracted with DCM
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-7aedf231f96e4fe5ab6740cafd189957
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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