Potassium Carbonate → HCID 117857251, compound

HRID 2276795Notes

Reaction equation

Cl.[CH3:2][O:3][C:4]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:5]=1[CH2:6][NH:7][C:8]([C:10]1[CH:24]=[CH:23][C:13]2[CH2:14][CH:15]3[CH:20]([CH3:21])[C:19]([CH3:22])([C:12]=2[CH:11]=1)[CH2:18][CH2:17][NH:16]3)=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH3:37][O:38][CH2:39][CH2:40]Br>C(#N)C>[CH3:2][O:3][C:4]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:5]=1[CH2:6][NH:7][C:8]([C:10]1[CH:24]=[CH:23][C:13]2[CH2:14][C@@H:15]3[C@H:20]([CH3:21])[C@:19]([CH3:22])([C:12]=2[CH:11]=1)[CH2:18][CH2:17][N:16]3[CH2:40][CH2:39][O:38][CH3:37])=[O:9]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 2R,6R,11R)—N-(2,4-dimethoxybenzyl)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocine-8-carboxamide hydrochloride (400 mg, 0.93 mmol), potassium carbonate (385 mg, 2.78 mmol), and bromoethyl methyl ether (142 mg, 1.02 mmol) in acetonitrile (15 mL) was heated at 65° C. overnight. Further bromoethyl methyl ether was added (70 mg, 0.50 mmol) and the reaction heated at 65° C. for 24 hours. The reaction mixture was allowed to return to ambient temperature before partitioning between ethyl acetate (100 mL) and water (100 mL). The organic phase was dried (MgSO4). Filtration and removal of the solvent under reduced pressure gave (2R,6R,11R)—N-(2,4-dimethoxybenzyl)-3-(2-methoxyethyl)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocine-8-carboxamide (360 mg, 86% yield); LC/MS (M+H)+=453.2.

Workup

temperaturethe reaction heated at 65° C. for 24 hours
customto return to ambient temperature
custombefore partitioning between ethyl acetate (100 mL) and water (100 mL)
dry with materialThe organic phase was dried (MgSO4)
filtrationFiltration and removal of the solvent under reduced pressure

Sources & evidence

ORD record: ord-8c1c4f0eaefd440f8f9fa3366c948975
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133125B2

Reaction notes

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