Diisopropylethylamine → Tert-butyl 4-(3-acetylbenzoyl)piperazine-1-carboxylate

HRID 1169602Notes

Reaction equation

HRID 1169602 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)(=[O:3])[CH3:2].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.N#N.CCOC(C)=O>[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([N:23]1[CH2:22][CH2:21][N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH2:25][CH2:24]1)=[O:9])(=[O:3])[CH3:2]

Participants

9

Reactant 5

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 181649HOAtHCID 2203243-Acetylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68765074Tert-butyl 4-(3-acetylbenzoyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 947NitrogenSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Acetylbenzoic acid (1.64 g, 10.0 mmol), 1-tert-butoxycarbonylpiperazine (2.23 g, 12.0 mmol), HATU (4.56 g, 12.0 mmol) and HOAT (1.63 g, 12.0 mmol) were dissolved in 20 mL anhydrous DMF in a 100 mL round-bottom flask under a positive pressure of N2 in an ice bath. DIPEA (3.8 mL, 22.0 mmol) was added and the mixture stirred at ambient temperature for 2 h. The solution was diluted with 100 mL of EtOAc and washed with 40 mL each: 0.2 N NaOH solution once and saturated NaCl solution twice. The organic layer was dried over Na2SO4, filtered, concentrated and purified by silica gel chromatography using EtOAc-hexanes (2:1 v/v) as the eluant to give tert-butyl 4-(3-acetylbenzoyl)piperazine-1-carboxylate as 2.97 g of white solid.

Workup

  1. washwashed with 40 mL each
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-ff85d2a9e8314203bd4c21c53f938649
Source dataset
uspto-grants-2010_11
Patent number
US07825120B2

Reaction notes

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