8-Methoxy-2,3,4,5,6,7-hexahydroazocine → HCID 11771845, compound

HRID 913047Notes

Reaction equation

[CH2:1]([C:6]12[CH2:13][CH2:12][C:9]([C:14]([NH:16][NH2:17])=O)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4][CH3:5].CO[C:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]=1>CN(C=O)C>[CH2:1]([C:6]12[CH2:13][CH2:12][C:9]([C:14]3[N:27]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20]4=[N:17][N:16]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 130 °C

Procedure

To 0.700 mL of the 0.3 M solution of 4-pentylbicyclo[2.2.2]octane-1-carbohydrazide in DMF (crude, prepared as in step A above) was added 8-methoxy-2,3,4,5,6,7-hexahydroazocine (29.6 mg, 1 eq) and the reaction was heated to 130° C. overnight. After this time the solvent was removed under reduced pressure and the residue was chromatographed on C-18 reverse phase (gradient 90% water to 100% acetonitrile, 0.1% TFA). The fractions containing the compound were determined by LCMS, added to 200 mL of methylene chloride, and extracted with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate and evaporated under diminished pressure. The residue was lyophilized from benzene to afford 3-(4-pentylbicyclo[2.2.2]oct-1-yl)-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (1-C); MS (ESI+)=300.3 (M+1)

Workup

customAfter this time the solvent was removed under reduced pressure
customthe residue was chromatographed on C-18 reverse phase (gradient 90% water to 100% acetonitrile, 0.1% TFA)
additionThe fractions containing the compound
additionadded to 200 mL of methylene chloride
extractionextracted with saturated sodium bicarbonate
dry with materialThe organic layer was dried over magnesium sulfate
customevaporated under diminished pressure

Sources & evidence

ORD record: ord-9a55fadb4d804f88b8be7ea9390abfc5
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026264B2

Reaction notes

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