Hydrochloric Acid → HCID 67006469, compound

HRID 564574Notes

Reaction equation

HRID 564574 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][C:5](=[CH:10][C:11]1[CH:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=3)[CH:14]=[CH:15][CH:16]=1)[CH2:6]2.[ClH:25]>CO.[OH-].[OH-].[Pd+2]>[ClH:25].[ClH:25].[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]([CH2:10][C:11]1[CH:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH2:24])[CH:18]=3)[CH:14]=[CH:15][CH:16]=1)[CH2:6]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 670056713'-[(8-Methyl-8-azabicyclo[3.2.1]oct-3-ylidene)methyl]-3-biphenylcarbonitrile

Product 1

HCID 67006469HCID 67006469, compoundYield 173%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3′-[(8-methyl-8-azabicyclo[3.2.1]oct-3-ylidene)methyl]-3-biphenylcarbonitrile (1.21 g, 3.85 mmol) in MeOH (192 mL) was added HCl (3.85 mL, 1N, 3.85 mmol). This mixture was then applied to an H-cube hydrogenation apparatus using 20% Pd(OH)2 cartridge at a flow rate of 1 mL/min. and H2 (1 atm) at 20° C. until reaction complete by monitoring with LC-MS. The reaction mixture was concentrated to afford 1.31 g (87%) of the title compound. LC-MS m/z 321 (M+H)+.

Workup

  1. customat 20° C.
  2. customuntil reaction complete
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-56f51836efb544abb875602333eb949e
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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