Ammonia → HCID 13409302, compound

HRID 536662Notes

Reaction equation

HRID 536662 reaction equation
[CH3:1][CH:2]1[N:9]([C:10]#N)[CH:8]2[CH2:12][C:4]([CH3:17])([C:5]3[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=3[CH2:7]2)[CH2:3]1.Cl.N>O>[CH3:10][N:9]1[CH:2]([CH3:1])[CH2:3][C:4]2([CH3:17])[CH2:12][CH:8]1[CH2:7][C:6]1[CH:13]=[CH:14][CH:15]=[CH:16][C:5]=12

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 86650494HCID 86650494, compound

Product 1

HCID 13409302HCID 13409302, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4,6-dimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocine-3-carbonitrile (one diastereomer, 925 mg), water (30 mL), and 4 M hydrochloric acid (30 mL) is stirred at reflux temperature for 9 h. After cooling to ambient temperature, the solution is basified using concentrated aqueous ammonia solution and the resulting mixture is extracted with EtOAc (2×50 mL). The combined organic extracts are washed with brine and dried (MgSO4). Removal of the solvent under reduced pressure affords the title compound.

Workup

  1. temperatureat reflux temperature for 9 h
  2. extractionthe resulting mixture is extracted with EtOAc (2×50 mL)
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-ce3769469d9a4164b8d227b6cdca123a
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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