Trifluoroacetic acid → Morpholin-3-ylmethyl 4-phenylpiperazine-1-carboxylate

HRID 2262508Notes

Reaction equation

HRID 2262508 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][CH:27]=[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>[C:24]1([N:21]2[CH2:22][CH2:23][N:18]([C:16]([O:15][CH2:14][CH:9]3[CH2:10][O:11][CH2:12][CH2:13][NH:8]3)=[O:17])[CH2:19][CH2:20]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 669345083-(4-Phenyl-piperazine-1-carbonyloxymethyl)-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 42634520Morpholin-3-ylmethyl 4-phenylpiperazine-1-carboxylateYield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(4-Phenyl-piperazine-1-carbonyloxymethyl)-morpholine-4-carboxylic acid tert-butyl ester (3.31 g, 8.16 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 solvents were removed in vacuo and the residue was partitioned between DCM (30 mL) and aq NaHCO3 (5 g in 30 mL). The aqueous layer was extracted with DCM (3×30 mL), dried (MgSO4) and the solvents were removed in vacuo to give morpholin-3-ylmethyl 4-phenylpiperazine-1-carboxylate (2.55 g, quant.) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-a27652104cda47cc9080ae6531f969b9
Source dataset
uspto-grants-2010_12
Patent number
US07851471B2

Reaction notes

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