Trifluoroacetic acid → Morpholin-3-ylmethyl 4-(4-fluorophenyl)piperazine-1-carboxylate

HRID 2262501Notes

Reaction equation

HRID 2262501 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][CH:25]=2)[CH2:20][CH2:19]1)=[O:17])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:30][C:27]1[CH:28]=[CH:29][C:24]([N:21]2[CH2:20][CH2:19][N:18]([C:16]([O:15][CH2:14][CH:9]3[CH2:10][O:11][CH2:12][CH2:13][NH:8]3)=[O:17])[CH2:23][CH2:22]2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 669345503-[4-(4-Fluorophenyl)-piperazine-1-carbonyloxymethyl]-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 42634358Morpholin-3-ylmethyl 4-(4-fluorophenyl)piperazine-1-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-[4-(4-Fluorophenyl)-piperazine-1-carbonyloxymethyl]-morpholine-4-carboxylic acid tert-butyl ester (2.98 g, 7.04 mmol) was stirred in DCM (30 mL) at 0° C. TFA (6 mL) dissolved in DCM (24 mL) was added dropwise. The reaction mixture was stirred overnight at room temperature. The solvent was removed in vacuo and the residue was partitioned between DCM (30 mL) and aqueous NaHCO3 (5 g in 30 mL). The aqueous layer was extracted with DCM (3×30 mL), dried (MgSO4) and the solvent removed in vacuo to give morpholin-3-ylmethyl 4-(4-fluorophenyl)piperazine-1-carboxylate (2.18 g, 96%) as a white solid.

Workup

  1. additionwas added dropwise
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between DCM (30 mL) and aqueous NaHCO3 (5 g in 30 mL)
  4. extractionThe aqueous layer was extracted with DCM (3×30 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-12ea62f0b67147749c144816fcdab60c
Source dataset
uspto-grants-2010_12
Patent number
US07851471B2

Reaction notes

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