4-Methylmorpholine → (4-Bromo-phenyl)-{4-(1-ethyl-propyl)-piperazin-1-yl}-methanone

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	4-Bromobenzoic acid	HCID 11464	—
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Reactant	686721-33-5	HCID 57478575	—
Solvent	Dichloromethane	HCID 6344	—
Product	(4-Bromo-phenyl)-{4-(1-ethyl-propyl)-piperazin-1-yl}-methanone	HCID 57478583	74.7%

Reaction Steps

To a solution of 4-bromobenzoic acid (500 mg) and the product of Example 7 (710 mg) in DCM (20 mL) was added 1-{3-(dimethylamino) propyl}-3-ethylcarbodiimide hydrochloride (713 mg), 1-hydroxybenzotriazole hydrate (570 mg), and N-methyl morpholine (1.64 mL). After 16 h the reaction mixture was treated with 1 N NaOH (25 mL) and extracted with DCM (3×75 mL). The organic layers were dried (Na2SO4), concentrated, and chromatographed on silica gel (1-3% 2 M methanolic ammonia/DCM) to give the title compound as white-yellow solid (630 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07414047B2
Source dataset	uspto-grants-2008_08
ORD ID	ord-ac3b941de28c42049e30f91eed7c7e71
Source note	uspto-grants-2008_08