Triethylamine → Tert-butyl 4-{4-[hydroxy(phenyl)methyl]benzoyl}piperazine-1-carboxylate

HRID 1180377Notes

Reaction equation

HRID 1180377 reaction equation
[OH:1][CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[N:18]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>CN(C=O)C>[OH:1][CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:21]2[CH2:20][CH2:19][N:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH2:22]2)=[O:9])=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2363614-[hydroxy(phenyl)methyl]benzoic acidHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 69470269Tert-butyl 4-{4-[hydroxy(phenyl)methyl]benzoyl}piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the crude compound of 4-[hydroxy(phenyl)methyl]benzoic acid (1.51 g, 6.6 mmol) in DMF (33 mL) was added tert-butyl piperazine-1-carboxylate (1.23 g, 6.6 mmol), triethylamine (3.7 mL, 26.5 mmol) and HATU (2.51 g, 6.6 mmol). The mixture was aged for 3 hours under a nitrogen atmosphere and was then poured into a saturated aqueous solution of NaHCO3. The resulting mixture was extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried and evaporated to a solid which was stirred in ethyl acetate at room temperature for 2 hours. The title compound was then recovered by filtration as a white solid.

Workup

  1. extractionThe resulting mixture was extracted 3 times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. customevaporated to a solid which
  5. filtrationThe title compound was then recovered by filtration as a white solid

Sources & evidence

ORD record
ord-09f99fdc2c2b48ef8e78c6f93ccdcd81
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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