Trifluoroacetic acid → 1-(4-Chloro-phenyl)-piperazine-2-carboxylic acid methyl ester

HRID 557048Notes

Reaction equation

HRID 557048 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]([CH:5]1[CH2:6][NH:7][CH2:8][CH2:9][N:10]1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66758208HCID 66758208, compound

Product 1

HCID 667581311-(4-Chloro-phenyl)-piperazine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-chloro-phenyl)-piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (0.4 g, 1.13 mmol) in dichloromethane (5.0 mL) cooled at 0° C. was treated with trifluoroacetic acid (20%) and warmed to room temperature and stirred for 2 h. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate and free based with 10% aqueous sodium bicarbonate. The combined organics were dried over sodium sulfate and concentrated. The product was used without any further purification. ESI-MS m/z: 254 (M+1), UV retention time: 1.01 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe product was used without any further purification

Sources & evidence

ORD record
ord-9f651673a19048a3980f3e1e40e59f06
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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