Hydrochloric Acid → 4-({3-[8-(Methylamino)-3-azabicyclo[3.2.1]oct-3-yl]propyl}amino)benzonitrile

HRID 411525Notes

Reaction equation

[C:1]([C:3]1[CH:29]=[CH:28][C:6]([NH:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:17][CH:16]3[CH:18]([N:19](C)[C:20](=O)[O:21]C(C)(C)C)[CH:13]([CH2:14][CH2:15]3)[CH2:12]2)=[CH:5][CH:4]=1)#[N:2].Cl>C(OCC)(=O)C>[OH-:21].[NH4+:2].[CH3:20][NH:19][CH:18]1[CH:13]2[CH2:14][CH2:15][CH:16]1[CH2:17][N:11]([CH2:10][CH2:9][CH2:8][NH:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:29][CH:28]=1)[CH2:12]2

Participants

Conditions

Temperature: 25 °C

Procedure

A suspension of tert-butyl 3-[3-(4-cyanoanilino)propyl]-3-azabicyclo-[3.2.1]oct-8-yl(methyl)carbamate (see step (iii) above; 2.66 g, 6.67 mmol) in ethyl acetate saturated with HCl (40 mL) was stirred overnight at 25° C. under nitrogen. The mixture was partitioned with water (100 mL) and ethyl acetate (50 mL). The aqueous layer was basified with saturated sodium bicarbonate (50 mL) and then extracted with dichloromethane (3×50 mL). The organic extracts were dried (Na2SO4), filtered, concentrated in vacuo and then chromatographed on silica gel, eluting with dichloromethane:methanol:concentrated ammonium hydroxide (92:7:1), to afford 1.07 g (54%) of the title compound as a white solid.

Workup

customThe mixture was partitioned with water (100 mL) and ethyl acetate (50 mL)
extractionextracted with dichloromethane (3×50 mL)
dry with materialThe organic extracts were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customchromatographed on silica gel
washeluting with dichloromethane

Sources & evidence

ORD record: ord-d815d06359ed42d9a9a8b5b1ba64fd70
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559162B2

Reaction notes

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