Acetaldehyde → HCID 20332939, compound

HRID 26428Notes

Reaction equation

HRID 26428 reaction equation
[CH:1]([NH:4][CH:5]([CH3:23])[CH2:6][C:7]1[C:8](=[O:22])[NH:9][CH2:10][CH2:11][CH2:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)([CH3:3])[CH3:2].[CH:24](=O)[CH3:25].C([BH3-])#N.[Na+].Cl>C(#N)C.C(O)(=O)C>[CH:1]([N:4]([CH:5]([CH3:23])[CH2:6][C:7]1[C:8](=[O:22])[NH:9][CH2:10][CH2:11][CH2:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[CH2:24][CH3:25])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 20332938HCID 20332938, compound

Product 1

HCID 20332939HCID 20332939, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

4.78 ml of glacial acetic acid are added dropwise to the ice-cooled mixture of 7.6 g of 3-(2-isopropylaminopropyl)-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone, 13.3 ml of acetaldehyde, 4.5 g of sodium cyanoborohydride and 90 ml of acetonitrile. The mixture is stirred at room temperature for 90 minutes, cooled in an ice-bath, acidified to pH=1 with concentrated hydrochloric acid and evaporated. The residue is taken up in 150 ml of water, the solution washed with diethyl ether, filtered, basified with 3 N aqueous sodium hydroxide and extracted with diethyl ether. The extract is dried, evaporated, the residue crystallized from petroleum ether and further purified by suspension in hexane, to yield the 3-[2-(N-isopropyl-N-ethylamino)-propyl]-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone melting at 64°-66°.

Workup

  1. temperaturecooled
  2. temperaturecooled in an ice-bath
  3. customevaporated
  4. washthe solution washed with diethyl ether
  5. filtrationfiltered
  6. extractionextracted with diethyl ether
  7. customThe extract is dried
  8. customevaporated
  9. customthe residue crystallized from petroleum ether
  10. customfurther purified by suspension in hexane

Sources & evidence

ORD record
ord-e1dfc62fc27d49f2884572f3fb81abb9
Source dataset
uspto-grants-1979_04
Patent number
US04150129

Reaction notes

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