Ethyl Acetate → HCID 13428535, compound

HRID 1638804Notes

Reaction equation

HRID 1638804 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6][Cl:7].C([N:17]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O>[ClH:7].[ClH:7].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6][N:17]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 70066561,4-diazepane-1-carbaldehyde

Product 1

HCID 13428535HCID 13428535, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3,4,5-trimethoxybenzyl chloride (10.5 g), N-formyl homopiperazine (6.82 g), potassium carbonate (8 g) and ethyl acetate (40 ml) is heated at 50-60° C. for 4 hours. After addition of water the reaction mixture is shaken thoroughly. The organic layer is separated, washed with water, dried and evaporated under reduced pressure. To the residue is added 10% hydrochloric acid (20 ml), and the mixture is extracted with ethyl acetate. The aqueous layer is made alkaline (>pH 9) with a 20% aqueous solution of sodium hydroxide, and extracted with methylene chloride. The extract solution is evaporated under reduced pressure. To the residue is added 10% hydrochloric acid (15 ml), and the mixture is stirred at 100° C. for 3 hours. The reaction mixture is made alkaline with a 20% aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The extract solution is dried and evaporated under reduced pressure. The residue is converted to the hydrochloride in a mixture of ethyl acetate and ethanol to yield 1-(3,4,5-trimethoxybenzyl) homopiperazine dihydrochloride (2.7 g) as colorless powdery crystals, m.p. 216°-220° C.

Workup

  1. customThe organic layer is separated
  2. washwashed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. additionTo the residue is added 10% hydrochloric acid (20 ml)
  6. extractionthe mixture is extracted with ethyl acetate
  7. extractionextracted with methylene chloride
  8. customThe extract solution is evaporated under reduced pressure
  9. additionTo the residue is added 10% hydrochloric acid (15 ml)
  10. stirringthe mixture is stirred at 100° C. for 3 hours
  11. extractionextracted with ethyl acetate
  12. customThe extract solution is dried
  13. customevaporated under reduced pressure
  14. additionThe residue is converted to the hydrochloride in a mixture of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-4ae78cdc6be4411cb8e1dd65d8c0dafe
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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