HCID 70374095, compound → HCID 70374350, compound

HRID 1032267Notes

Reaction equation

HRID 1032267 reaction equation
C([CH:3]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH2:16][C:10]3[C:11]2=[C:5]([CH2:6][N:7]=[CH:8][CH:9]=3)[CH2:4]1)#N>C(O)(=O)C.Cl>[CH2:13]1[CH:12]2[CH2:14][CH2:15][CH2:16][C:10]3[C:11]2=[C:5]([CH2:6][N:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 70374095HCID 70374095, compound

Product 1

HCID 70374350HCID 70374350, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1.3 g (6.1 mmol) of 2-cyano-1,2,3,4,8,9,10,10a-octahydronaphth[1,8-cd]azepine, an intermediate of Formula 8 prepared, for example, as described in Preparation 8A, in a mixture of 40 ml of acetic acid and 40 ml of 20% hydrochloric acid, was kept at reflux for 20 hours. The solution was concentrated to a small volume, approximately 30 ml of water was added and neutral materials were removed by extraction with ether. The aqueous layer was made basic by addition of NaOH, and the product was extracted with ether. After evaporation of the ether, 0.8 g of 1,2,3,4,8,9,10,10a-octahydronaphth[1,8-cd]azepine was obtained as an oil (HCl salt, mp 207°-209° C.).

Workup

  1. temperatureat reflux for 20 hours
  2. concentrationThe solution was concentrated to a small volume, approximately 30 ml of water
  3. additionwas added
  4. customneutral materials were removed by extraction with ether
  5. additionThe aqueous layer was made basic by addition of NaOH
  6. extractionthe product was extracted with ether
  7. customAfter evaporation of the ether

Sources & evidence

ORD record
ord-1a4c443c4fe44fffbf875a611de8b22f
Source dataset
uspto-grants-1990_09
Patent number
US04957914

Reaction notes

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