Trifluoroacetic acid → Morpholin-3-ylmethyl 4-(2,4-difluorophenyl)piperazine-1-carboxylate

HRID 2262510Notes

Reaction equation

HRID 2262510 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]1[CH2:14][O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[F:31])[CH2:20][CH2:19]1)=[O:17])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[N:21]1[CH2:20][CH2:19][N:18]([C:16]([O:15][CH2:14][CH:9]2[CH2:10][O:11][CH2:12][CH2:13][NH:8]2)=[O:17])[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 669345373-[4-(2,4-Difluoro-phenyl)-piperazine-1-carbonyloxymethyl]-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 42634521Morpholin-3-ylmethyl 4-(2,4-difluorophenyl)piperazine-1-carboxylateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-[4-(2,4-difluoro-phenyl)-piperazine-1-carbonyloxymethyl]-morpholine-4-carboxylic acid tert-butyl ester (170 mg, 0.39 mmol) in DCM (5 mL) at 0° C. was added TFA (1 mL in 5 mL DCM). The reaction mixture was allowed to warm to room temperature and stirred overnight. The solvent was removed in vacuo and the residue suspended between sat aq NaHCO3 (10 mL) and DCM (10 mL). The aqueous phase was extracted with DCM (2×10 mL). The combined organic layers were dried (MgSO4) and the solvent removed in vacuo to give morpholin-3-ylmethyl 4-(2,4-difluorophenyl)piperazine-1-carboxylate (104 mg, 79%) as a colourless oil.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionThe aqueous phase was extracted with DCM (2×10 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ea3aa07249104d4b9ae9a0a7e629e8ca
Source dataset
uspto-grants-2010_12
Patent number
US07851471B2

Reaction notes

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