Benzyl Bromide → 1,1-Dimethylethyl 5-[cis-3,5-dimethyl-4-(phenyl methyl)-1-piperazinyl]-2-(methyloxy)-3-pyridinecarboxylate

HRID 2234989Notes

Reaction equation

[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[C:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:12]([O:15][CH3:16])=[N:13][CH:14]=2)[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C)C=O>[CH3:8][C@H:6]1[N:7]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]2[CH:10]=[C:11]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[C:12]([O:15][CH3:16])=[N:13][CH:14]=2)[CH2:5]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1,1-dimethylethyl 5-[cis-3,5-dimethyl-1-piperazinyl]-2-(methyloxy)-3-pyridinecarboxylate (D24) (500 mg, 1.56 mmol), potassium carbonate (430 mg, 3.12 mmol) and benzyl bromide (266 mg, 1.56 mmol) in N,N-dimethylformamide (10 ml) was stirred at 80° C. for 4 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic phase washed with water, dried and evaporated. Purification by flash chromatography eluting with 5-20% ethyl acetate in hexanes gave the title compound (D25). MS (ES+) m/e 412 [M+H]+.

Workup

customThe reaction mixture was partitioned between ethyl acetate and water
washThe organic phase washed with water
customdried
customevaporated
customPurification by flash chromatography
washeluting with 5-20% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-1e90daec7e784579a0de9945d44a2a72
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713978B2

Reaction notes

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