1-Isopropylpiperazine → HCID 68880149, compound

HRID 493175Notes

Reaction equation

HRID 493175 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([C:19]([OH:21])=O)=[CH:16][C:15]=3[CH:22]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH:23]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([CH3:25])[CH3:24].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>C1COCC1>[CH:23]([N:26]1[CH2:31][CH2:30][N:29]([C:19]([C:17]2[O:18][C:14]3[CH:13]=[CH:12][C:11]([O:10][CH:7]4[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:9][CH2:8]4)=[CH:22][C:15]=3[CH:16]=2)=[O:21])[CH2:28][CH2:27]1)([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 780131-IsopropylpiperazineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 68724847HCID 68724847, compound

Product 1

HCID 68880149HCID 68880149, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a flask were mixed together the above prepared 5-(1-isopropyl-piperidin-4-yloxy)-benzofuran-2-carboxylic acid (0.220 g, 0.549 mmol, corrected for purity), 1-isopropylpiperazine (0.084 g, 1.2 eq.), (benzotriazol-1-yloxy)-tris-(dimethylamino)-phosphonium hexafluorophosphate (0.291 g, 1.2 eq.) and 2.4 eq. of N-ethyldiisopropyl-amine (0.225 mL) in 2.2 mL of abs. THF and allowed to react during one night at ambient temperature. Pouring onto crashed ice/AcOEt/NH4Cl-solution, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, NEt3/AcOEt=4/96) produced 0.127 g of the title compound as light yellow oil.

Workup

  1. additionIn a flask were mixed together the
  2. customto react during one night at ambient temperature
  3. additionPouring
  4. extractionextraction with AcOEt
  5. washwashing with water
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-a17e6bd64646454081783c3ed145801f
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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