Trifluoroacetic acid → (R)-1-(3-methylpiperazin-1-yl)ethanone 2,2,2-trifluoroacetate

HRID 80755Notes

Reaction equation

HRID 80755 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[C@H:6]([CH3:17])[CH2:5]1)(=[O:3])[CH3:2].[C:18]([OH:24])([C:20]([F:23])([F:22])[F:21])=[O:19]>C(Cl)Cl>[F:21][C:20]([F:23])([F:22])[C:18]([OH:24])=[O:19].[CH3:17][C@H:6]1[NH:7][CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86690247HCID 86690247, compound

Product 1

HCID 86690248(R)-1-(3-methylpiperazin-1-yl)ethanone 2,2,2-trifluoroacetateYield 137.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-tert-butyl 4-acetyl-2-methylpiperazine-1-carboxylate (1.34 g, 5.53 mmol) and TFA (10 mL, 130 mmol) in DCM (30 mL) was stirred at rt for 45 min, then concentrated, diluted with DCM, and then concentrated again which was repeated 3 times. Dried under high vacuum at 80° C. to give (R)-1-(3-methylpiperazin-1-yl)ethanone 2,2,2-trifluoroacetate (1.95 g). MS (ESI+) m/z 143.0 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additiondiluted with DCM
  3. concentrationconcentrated again which
  4. customDried under high vacuum at 80° C.

Sources & evidence

ORD record
ord-70d07e067fa340f483a5e47aede96369
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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