4-Formylbenzoic acid → Tert-butyl 4-(4-formylbenzoyl)piperazine-1-carboxylate

HRID 13554

Reaction equation

HRID 13554 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=O.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:1](=[O:3])[C:4]2[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 120884-Formylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 59218188Tert-butyl 4-(4-formylbenzoyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-carboxybenzaldehyde (3.10 g) in CH2Cl2 was treated sequentially with piperazine-1-carboxylic acid tert-butyl ester (3.6 g), EDCl (3.86 g), HOBt (2.68 g), and 4-dimethylaminopyridine (˜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 yield the title compound.

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-9f2266dfe35b4b34a5f82d1e7a0771b8
Source dataset
uspto-grants-2010_06
Patent number
US07728129B2

Linked notes

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