Trifluoroacetic acid → Bavisant

HRID 604257Notes

Reaction equation

HRID 604257 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[O:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:22](OC(N1CCN(C(=O)C2C=CC(CN3CCOCC3)=CC=2)CC1)=O)([CH3:25])(C)[CH3:23].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:25]1([N:19]2[CH2:18][CH2:17][N:16]([C:14]([C:11]3[CH:10]=[CH:9][C:8]([CH2:7][N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)=[CH:13][CH:12]=3)=[O:15])[CH2:21][CH2:20]2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 592181854-(4-Morpholin-4-ylmethyl-benzoyl)piperazine-1-carboxylic acid tert-butyl esterHCID 59218186(4-Morpholin-4-ylmethyl-phenyl)piperazin-1-yl-methanone

Product 1

HCID 16061509BavisantYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Morpholin-4-ylmethyl-phenyl)-piperazin-1-yl-methanone. 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 TFA (˜4 mL). After 30 min, additional TFA (5 mL) was added, and the mixture was stirred for a further 2 h. The mixture was diluted with diluted with satd. aq. NaHCO3 and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by column chromatography (SiO2) to give the title compound (0.255 g, 30%). MS (ESI): mass calcd. for C16H23N3O2, 289.18; m/z found, 290.4 [M+H]+. 1H NMR (CDCl3): 7.41-7.35 (m, 4H), 3.95-3.70 (m, 6H), 3.52 (s, 2H), 3.09-2.80 (m, 6H), 2.49-2.42 (m, 4H).

Workup

  1. additionThe mixture was diluted
  2. additionwith diluted with satd
  3. extractionaq. NaHCO3 and extracted with CH2Cl2
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-c01190cbecf44e2f952b206f842e7bf7
Source dataset
uspto-grants-2011_03
Patent number
US07910582B2

Reaction notes

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