Acetic Acid → HCID 13477125, compound

HRID 370589Notes

Reaction equation

HRID 370589 reaction equation
[ClH:1].[O:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][O:6][C:5]2[CH:14]=[CH:15][C:16]([CH2:18][CH2:19]N)=[CH:17][C:4]1=2.[BH3-][C:22]#[N:23].[Na+].[C:25](O)(=O)C>C(#N)C.C=O>[ClH:1].[O:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][O:6][C:5]2[CH:14]=[CH:15][C:16]([CH2:18][CH2:19][N:23]([CH3:22])[CH3:25])=[CH:17][C:4]1=2

Participants

6

Reactant 3

HCID 176Acetic Acid2×HCID 5003444Sodium cyanoborohydrideHCID 13477123HCID 13477123, compound

Product 1

HCID 13477125HCID 13477125, compound

Reagents, catalysts & solvents 2

HCID 712FormaldehydeSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2.8 g (0.011 m) of 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethylamine of Example 6 in 60 ml of acetonitrile and 2.7 ml of 37% aqueous formaldehyde (0.1 m), 2.05 g (0.033 m) of NaBH3CN was added. There was a slightly exothermic reaction. Glacial acetic acid (2 ml) was added over 10 minutes and the reaction was stirred at ambient temperature for 2 hours. An additional 2 ml of glacial acetic acid was added and stirring was continued for 30 minutes. The solvent was evaporated under reduced pressure and the residue was treated with 60 ml of 2N KOH. The resulting mixture was extracted three times with ether. The combined ether extracts were washed with 60 ml of 0.5N KOH and then extracted three times with 1N HCl. The aqueous acidic extracts were combined and neutralized with solid KOH and then extracted with ether. The dried (Na2SO4) organic phase was filtered and ethereal HCl was added to precipitate 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)-N,N-dimethylethylamine hydrochloride, 1.4 g (40%), m.p. 175°-176° C.

Workup

  1. customa slightly exothermic reaction
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. customThe solvent was evaporated under reduced pressure
  5. additionthe residue was treated with 60 ml of 2N KOH
  6. extractionThe resulting mixture was extracted three times with ether
  7. washThe combined ether extracts were washed with 60 ml of 0.5N KOH
  8. extractionextracted three times with 1N HCl
  9. extractionextracted with ether
  10. dry with materialThe dried (Na2SO4) organic phase
  11. filtrationwas filtered
  12. additionethereal HCl was added
  13. customto precipitate 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)-N,N-dimethylethylamine hydrochloride, 1.4 g (40%), m.p. 175°-176° C.

Sources & evidence

ORD record
ord-104da1f5d99d48b58f3ada0acb4f8524
Source dataset
uspto-grants-1985_07
Patent number
US04526891

Reaction notes

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