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

HRID 2218985Notes

Reaction equation

HRID 2218985 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.Cl.Cl.[CH2:13]([CH:15]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH2:16][CH3:17])[CH3:14].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:21]2[CH2:22][CH2:23][N:18]([CH:15]([CH2:16][CH3:17])[CH2:13][CH3:14])[CH2:19][CH2:20]2)=[O:8])=[CH:9][CH:10]=1

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 114644-Bromobenzoic acidHCID 14798Sodium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57478575686721-33-5

Product 1

HCID 57478583(4-Bromo-phenyl)-{4-(1-ethyl-propyl)-piperazin-1-yl}-methanoneYield 74.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  1. extractionextracted with DCM (3×75 mL)
  2. dry with materialThe organic layers were dried (Na2SO4)
  3. concentrationconcentrated
  4. customchromatographed on silica gel (1-3% 2 M methanolic ammonia/DCM)

Sources & evidence

ORD record
ord-ac3b941de28c42049e30f91eed7c7e71
Source dataset
uspto-grants-2008_08
Patent number
US07414047B2

Reaction notes

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