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

HRID 411525
Notes
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Reaction equation

HRID 411525 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18540877Tert-butyl 3-[3-(4-cyanoanilino)propyl]-3-azabicyclo[3.2.1]oct-8-yl-(methyl)carbamate

Product 2

HCID 14923Ammonium HydroxideHCID 185408864-({3-[8-(Methylamino)-3-azabicyclo[3.2.1]oct-3-yl]propyl}amino)benzonitrileYield 107.5%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

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

  1. customThe mixture was partitioned with water (100 mL) and ethyl acetate (50 mL)
  2. extractionextracted with dichloromethane (3×50 mL)
  3. dry with materialThe organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes