Hydrochloric Acid → HCID 21448614, compound

HRID 596869Notes

Reaction equation

HRID 596869 reaction equation
C[C:2]([CH3:24])([CH:7]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[NH:8][CH2:9][CH2:10][C:11]([O:13]C)=O)[C:3](OC)=O.[CH2:25]([Cl:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl>C(C(C)=O)C>[ClH:32].[CH2:25]([N:8]1[CH2:9][CH2:10][C:11](=[O:13])[C:2]([CH3:3])([CH3:24])[CH:7]1[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 21448601HCID 21448601, compound

Product 1

HCID 21448614HCID 21448614, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 24.5 g of crude dimethyl 2,2-dimethyl-3-(p-methoxybenzyl)-3,3'-iminodipropionate, 27 g of benzyl chloride, 23 g of potassium iodide, 40 g of potassium carbonate and 300 ml of methyl ethyl ketone is refluxed and stirred during 35 hours. The mixture is cooled and evaporated in vacuo whereupon the residue is treated with chloroform. Inorganic material is removed by filtration and the filtrate is concentrated in vacuo leaving a residue which is shaken with 300 ml of 4 N hydrochloric acid and 100 ml of petroleum ether in order to remove neutral products. After basification with aqueous ammonia, the N-benzyl-2,2-dimethyl-3-(p-methoxybenzyl)-3,3'-iminodipropionic acid dimethylester is extracted from the mixture by shaking with chloroform. It is obtained in nearly quantitative yield, and, without purification submitted to a Dieckmann cyclization using 5.2 g of sodium hydride (50% dispersion in oil) and 200 ml of dimethylformamide. Further processing is carried out according to the directions already described in preceding examples, giving the above-mentioned product which is recrystalized from ethanol/ether. Yield 35%. Melting point 161° - 162° C, with decomposition.

Workup

  1. temperatureis refluxed
  2. temperatureThe mixture is cooled
  3. customevaporated in vacuo whereupon the residue
  4. additionis treated with chloroform
  5. customInorganic material is removed by filtration
  6. concentrationthe filtrate is concentrated in vacuo
  7. customleaving a residue which
  8. customto remove neutral products
  9. extractionAfter basification with aqueous ammonia, the N-benzyl-2,2-dimethyl-3-(p-methoxybenzyl)-3,3'-iminodipropionic acid dimethylester is extracted from the mixture
  10. stirringby shaking with chloroform
  11. customIt is obtained in nearly quantitative yield
  12. customwithout purification
  13. customgiving the above-mentioned product which
  14. customis recrystalized from ethanol/ether

Sources & evidence

ORD record
ord-ec9cb30d76a5416aaba168d184ca420f
Source dataset
uspto-grants-1977_03
Patent number
US04012392

Reaction notes

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