Trifluoroacetic acid → HCID 57657633, compound

HRID 1514387Notes

Reaction equation

HRID 1514387 reaction equation
[F:1][C:2]1([F:24])[CH2:7][CH2:6][CH:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][C@H:11]2[CH3:23])=[O:9])[CH2:4][CH2:3]1.FC(F)(F)C(O)=O.C([O-])([O-])=O.[K+].[K+]>ClCCl>[F:24][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][C@@H:11]2[CH3:23])=[O:9])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 68937938HCID 68937938, compound

Product 1

HCID 57657633HCID 57657633, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-butyl 4-(4,4-difluorocyclohexanecarbonyl)-3-methylpiperazine-1-carboxylate 54 (1.89 g, 5.46 mmol) was dissolved in dichloromethane (30 ml). Trifluoroacetic acid (4.20 ml, 54.6 mmol) was added and the reaction stirred at RT for 1.5 hours. The reaction was added to aqueous K2CO3 (100 ml) and extracted three times with dichloromethane (50 ml). The combined organic extracts were dried (MgSO4) and evaporated to give (S)-(4,4-difluorocyclohexyl)(2-methylpiperazin-1-yl)methanone 55 as a yellow oil, 1.35 g. LC/MS m/z=247 (M+H+).

Workup

  1. extractionextracted three times with dichloromethane (50 ml)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-33971a8630e64096b53fd6e75be0beac
Source dataset
uspto-grants-2012_07
Patent number
US08222251B2

Reaction notes

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