Hydrochloric Acid → HCID 1074708, compound

HRID 2109653Notes

Reaction equation

HRID 2109653 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6]Cl.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.Cl>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][N:13]1[CH2:18][CH2:17][N:16]([CH2:6][C:5]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 81740Veratryl chloride

Product 1

HCID 1074708HCID 1074708, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
97.5 °C

Procedure

3,4-dimethoxybenzyl chloride (10 g, 53.6 mmol) was combined with piperazine (2.3 g, 26.8 mmol) in anhydrous DMF (30 ml) and heated with stirring under nitrogen for 8 hours at 95-100° C. The cooled reaction mixture was diluted with water (100 ml) and acidified to pH 1 with concentrated hydrochloric acid. The white precipitate was collected by filtration and washed with water (50 ml). The solid was resuspended in water (50 ml) and the pH adjusted to >9 by the dropwise addition of sodium hydroxide solution (50% NaOH in water). The resultant white solid was collected by filtration and dried under vacuum at 50° C., yield 10 g.

Workup

  1. temperatureheated
  2. customThe cooled reaction mixture
  3. filtrationThe white precipitate was collected by filtration
  4. washwashed with water (50 ml)
  5. additionthe pH adjusted to >9 by the dropwise addition of sodium hydroxide solution (50% NaOH in water)
  6. filtrationThe resultant white solid was collected by filtration
  7. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-09c18d5880684bc08aa4bc49bd81b96d
Source dataset
uspto-grants-2009_04
Patent number
US07514583B2

Reaction notes

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