Hydrochloric Acid → 4-{2-[8-(Methylamino)-3-azabicyclo[3.2.1]oct-3-yl]ethoxy}benzonitrile

HRID 411535Notes

Reaction equation

HRID 411535 reaction equation
Cl.[C:2]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH2:17][CH:16]3[CH:18]([N:19](C)[C:20](=O)OC(C)(C)C)[CH:13]([CH2:14][CH2:15]3)[CH2:12]2)=[CH:6][CH:5]=1)#[N:3]>C(OCC)(=O)C>[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][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:29][CH:28]=1)[CH2:12]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18540898Tert-butyl 3-[2-(4-cyanophenoxy)ethyl]-3-azabicyclo[3.2.1]oct-8-yl-(methyl)carbamate

Product 1

HCID 185408764-{2-[8-(Methylamino)-3-azabicyclo[3.2.1]oct-3-yl]ethoxy}benzonitrileYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Ethyl acetate (30 mL) saturated with gaseous HCl was added to a solution of tert-butyl 3-[2-(4-cyanophenoxy)ethyl]-3-azabicyclo[3.2.1]oct-8-yl-(methyl)carbamate (see step (ii) above; 1.1 g, 2.8 mmol) in ethyl acetate at 0° C. The resulting mixture was stirred for 4 h at rt. The solvent was removed in vacuo before MeCN (29 mL), water (1.5 mL) and K2CO3 (2.4 g) were added. The resulting mixture was stirred overnight before being filtered, washed with CHCl3 and then concentrated in vacuo to give 0.79 g (99%) of the tide compound.

Workup

  1. customat 0° C
  2. customThe solvent was removed in vacuo before MeCN (29 mL), water (1.5 mL) and K2CO3 (2.4 g)
  3. additionwere added
  4. stirringThe resulting mixture was stirred overnight
  5. filtrationbefore being filtered
  6. washwashed with CHCl3
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11951e0aac5948cea4b7aa34376da392
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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