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HRID604255

反应详情

EQUATION

反应方程式

HRID 604255 的结构方程式

REACTANTS

反应物

4
结构：O=Cc1ccc(C(=O)O)cc1
HCID12088

4-Carboxybenzaldehyde

C8H6O3

结构：On1nnc2ccccc21
HCID75771

1-Hydroxybenzotriazole

C6H5N3O

结构：CC(C)(C)OC(=O)N1CCNCC1
HCID143452

tert-Butyl piperazine-1-carboxylate

C9H18N2O2

结构：CC(C)(C)OC(=O)N1CCN(C(=O)c2ccc(C=O)cc2)CC1
HCID59218188

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

C17H22N2O4

PRODUCTS

生成物

1
结构：O=C(c1ccc(CN2CCOCC2)cc1)N1CCN(C2CC2)CC1
HCID16061509

(4-Cyclopropylpiperazin-1-yl)(4-(morpholin-4-ylmethyl)phenyl)methanone

C19H27N3O2

收率 78%

AUXILIARIES

试剂、催化剂与溶剂

3
结构：CN(C)c1ccncc1
催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

结构：ClCCCl
溶剂HCID11

1,2-Dichloroethane

C2H4Cl2

结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

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

后处理

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