Ammonia → HCID 66893029, compound

HRID 1161997Notes

Reaction equation

HRID 1161997 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]4[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]4)[CH:12]=3)=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH3:19]>CO.CO.N>[N:13]12[CH2:18][CH2:17][CH:16]([CH2:15][CH2:14]1)[C:11]([C:8]1[O:9][C:10]3[C:2]([NH2:19])=[CH:3][CH:4]=[CH:5][C:6]=3[CH:7]=1)=[CH:12]2

Participants

5

Reactant 2

HCID 222AmmoniaHCID 10425107HCID 10425107, compound2×

Product 1

HCID 66893029HCID 66893029, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21705897Ammonia methanolSolvent

Conditions

Temperature
120 °C

Procedure

3-(7-Bromo-1-benzofuran-2-yl)-1-azabicyclo[2.2.2]oct-2-ene (300 mg, 0.986 mmol; Intermediate 25) was dissolved in methanol (2 mL). A solution of concentrated aqueous ammonia (25%; 10 mL) and CuCl2 (15 mg) were added and the resulting mixture was heated at 120° C. for 48 h. The mixture was run through a silica plug using methanol/ammonia solution (9:1) as eluent. Concentration in vacuo furnished 236 mg of the crude title product. This material was used directly in subsequent experiments.

Workup

  1. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-aff49bf7db1445d4bedc5c73b1cb366b
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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