Hydrochloric Acid → HCID 21332725, compound

HRID 1629966Notes

Reaction equation

HRID 1629966 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=O)[CH2:12][CH2:13][N:14](C)C)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.O.[NH2:20]N>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:12][CH2:13][NH:14][N:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 211864HCID 211864, compound

Product 1

HCID 21332725HCID 21332725, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A 100 mL round bottom flask equipped with a stir bar, Vigreux column and nitrogen inlet was charged with 1-(3,4-dimethoxy-phenyl)-3-dimethylamino-propan-1-one.HCl, (1.4 g, 5 mmol) EtOH, (20 mL) and hydrazine monohydrate, (0.3 mL, 6 mmol). The mixture was heated at 80° C. for 2 h. LC-MS and TLC analysis showed consumption of SM. The solvent was evaporated under reduced pressure and trace hydrazine and EtOH was removed under high vacuum for 30 min. The material was used as in the next step. Amount obtained 1030 mg, 5 mmol, 100% yield. LC-MS (ESI) m/e 207 (M+H). Step 3

Workup

  1. customA 100 mL round bottom flask equipped with a stir bar
  2. customconsumption of SM
  3. customThe solvent was evaporated under reduced pressure
  4. customwas removed under high vacuum for 30 min
  5. customAmount obtained 1030 mg, 5 mmol, 100% yield

Sources & evidence

ORD record
ord-022a942b04634889953701b3411dad53
Source dataset
uspto-grants-2014_07
Patent number
US08791114B2

Reaction notes

Loading…