Trifluoroacetic acid → (4-Morpholin-4-ylmethyl-phenyl)piperazin-1-yl-methanone

HRID 560992Notes

Reaction equation

HRID 560992 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:28])[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[N:22]1([CH2:21][C:18]2[CH:17]=[CH:16][C:15]([C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[O:28])=[CH:20][CH:19]=2)[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 592181854-(4-Morpholin-4-ylmethyl-benzoyl)piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59218186(4-Morpholin-4-ylmethyl-phenyl)piperazin-1-yl-methanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 4-(4-morpholin-4-ylmethyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester (1.163 g) in CH2Cl2 (10 mL) was treated with trifluoroacetic acid (˜4 mL). After 30 min, additional trifluoroacetic acid (5 mL) was added, and the mixture was stirred for a further 2 h. The mixture was diluted with diluted with saturated aquoues NaHCO3 and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by column chromatography (SiO2) to yield the title compound.

Workup

  1. additionThe mixture was diluted
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-34365dd70b7d4d7e8b977cf9f6272dd1
Source dataset
uspto-grants-2011_11
Patent number
US08063206B2

Reaction notes

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