Hydrochloric Acid → HCID 53996374, compound

HRID 1905829Notes

Reaction equation

HRID 1905829 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:19])[CH2:17][CH3:18])=[CH:11][CH:10]=1)[CH3:6])[CH3:2].C([BH3-])#N.[Na+].Cl>C(O)C>[CH2:1]([O:3][NH:4][CH:5]([CH3:6])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:16]([CH3:19])[CH2:17][CH3:18])=[CH:13][CH:14]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 53778288HCID 53778288, compound

Product 1

HCID 53996374HCID 53996374, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4-[4-(1-methylpropoxy)phenyl]-2-butanone O-ethyloxime (2.63 g, 10.0 mmol) in 30 ml of ethanol is added sodium cyanoborohydride (2.00 g, 38.1 mmol) and methanolic 2N HCl is added throughout the reaction to maintain pH at 3. The reaction temperature is maintained at 15°-20°. After ca. 2 hours, the solvent is removed under vacuum. The mixture is made basic by the addition of 10% sodium hydroxide, followed by water and ether, and is extracted with ether. The combined organic phases are washed with water and with brine, dried and filtered and the solvent is removed in vacuo to give N-ethoxy-1-methyl-3-[4-(1-methylpropoxy)phenyl]propylamine, MS m/e 265 (M ).

Workup

  1. additionis added throughout the reaction
  2. temperatureto maintain pH at 3
  3. temperatureThe reaction temperature is maintained at 15°-20°
  4. customthe solvent is removed under vacuum
  5. additionThe mixture is made basic by the addition of 10% sodium hydroxide
  6. extractionis extracted with ether
  7. washThe combined organic phases are washed with water and with brine
  8. customdried
  9. filtrationfiltered
  10. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-0242feac310f4ac4a0df8cfa35c7ceed
Source dataset
uspto-grants-1987_03
Patent number
US04647698

Reaction notes

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