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

HRID 1743708Notes

Reaction equation

HRID 1743708 reaction equation
C([N:8]1[CH2:14][CH:13]2[N:15]([CH2:16][CH2:17][CH2:18][NH:19][C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=3)[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)C1C=CC=CC=1.Cl.C(Cl)Cl>C(#N)C>[CH:10]12[N:15]([CH2:16][CH2:17][CH2:18][NH:19][C:20]3[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=3)[CH:13]([CH2:12][CH2:11]1)[CH2:14][NH:8][CH2:9]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 222354174-{[3-(3-Benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)propyl]amino}benzonitrile

Product 1

HCID 222354684-{[3-(3,8-Diazabicyclo[3.2.1]oct-8-yl)propyl]amino}benzonitrileYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a cold solution of 4-{[3-(3-benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)propyl]amino}benzonitrile (6.26 g, 17.4 mmol; from step (c) above) in acetonitrile (100 mL) was added 12 M HCl (5.8 mL). The reaction mixture was stirred for 15 minutes, concentrated in vacuo and dried under high vacuum overnight. The resulting hydrochloride salt was added to a suspension of 10% Pd/C (800 mg) in methanol (250 mL). The reaction was then stirred under hydrogen (1 atmosphere of pressure) for 50 min. The mixture was filtered through Celite® and the filtrate was concentrated in vacuo. The resulting residue was partitioned with saturated NaHCO3 (100 mL) and CH2Cl2 (200 mL). The organic layer was dried (Na2SO4), filtered and concentrated ill vacuo to give the crude product. Flash chromatography on silica gel eluting with a gradient of CH2Cl2:CMA (4:1 to 2:1) gave 2.02 g (43%) of the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customdried under high vacuum overnight
  3. additionThe resulting hydrochloride salt was added to a suspension of 10% Pd/C (800 mg) in methanol (250 mL)
  4. stirringThe reaction was then stirred under hydrogen (1 atmosphere of pressure) for 50 min
  5. filtrationThe mixture was filtered through Celite®
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resulting residue was partitioned with saturated NaHCO3 (100 mL) and CH2Cl2 (200 mL)
  8. dry with materialThe organic layer was dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated ill vacuo
  11. customto give the crude product

Sources & evidence

ORD record
ord-55fe62d903f04c48888498c14a7e6246
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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