Benzoic Acid → 1-Piperazinecarboxylic acid, 4-benzoyl-, 1,1-diMethylethyl ester

HRID 1622324Notes

Reaction equation

HRID 1622324 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:14](O)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:14]([N:11]1[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 185197561-Piperazinecarboxylic acid, 4-benzoyl-, 1,1-diMethylethyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

General procedure A was followed using 1-Boc-piperazine (50 mg, 0.27 mmol), benzoic acid (43 mg, 0.35 mmol), HATU (0.14 g, 0.35 mmol), DIPEA (0.23 ml 1.4 mmol) and DMF (2 mL) to furnish the title compound as a beige solid (75 mg, 98%), m.p. 105-107° C.; umax (CHCl3)/cm−1 3011, 2930, 2866, 1691, 1626, 1421, 1249, 1158; m/z (ESI) C16H22N2NaO3 requires 313.1523, found [M+Na]+ 313.1528.

Sources & evidence

ORD record
ord-e95501e722794bac974c453eb37e2331
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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