4-Formylbenzoic acid → Bavisant

HRID 604255Notes

Reaction equation

HRID 604255 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(C1C=C[C:30]([CH:31]=[O:32])=CC=1)(O)=O.C(OC([N:42]1CCN[CH2:44][CH2:43]1)=O)(C)(C)C.[CH:48]1C=CC2N(O)N=NC=2[CH:53]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(Cl)CCl>[CH:6]1([N:8]2[CH2:9][CH2:10][N:11]([C:14]([C:15]3[CH:16]=[CH:17][C:18]([CH2:21][N:42]4[CH2:30][CH2:31][O:32][CH2:44][CH2:43]4)=[CH:19][CH:20]=3)=[O:23])[CH2:12][CH2:13]2)[CH2:53][CH2:48]1

Participants

8

Reactant 4

HCID 120884-Formylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 59218188Tert-butyl 4-(4-formylbenzoyl)piperazine-1-carboxylate

Product 1

HCID 16061509BavisantYield 78%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

4-(4-Formyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester. A suspension of 4-carboxybenzaldehyde (3.10 g) in CH2Cl2 was treated sequentially with piperazine-1-carboxylic acid tert-butyl ester (3.6 g), EDC (3.86 g), HOBt (2.68 g), and DMAP (˜0.020 g). After 18 h, the mixture was extracted with 1 N NaOH and then with 1 N HCl. The organic layer was dried (Na2SO4) and concentrated to give the title compound (5.11 g, 78%). MS (ESI): mass calcd. for C17H22N2O4, 318.16; m/z found, 219.3 [(M−100)+H]+. 1H NMR (CDCl3): 10.04 (s, 1H), 7.93 (d, J=8.2, 2H), 7.54 (d, J=8.1, 2H), 3.82-3.67 (m, 2H), 3.58-3.30 (m, 6H), 1.46 (s, 9H).

Workup

  1. extractionthe mixture was extracted with 1 N NaOH
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5371445e1bab432aaa56ce271c65de02
Source dataset
uspto-grants-2011_03
Patent number
US07910582B2

Reaction notes

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