Isopropylamine → HCID 19826633, compound

HRID 330457Notes

Reaction equation

HRID 330457 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH2:6][NH:7][CH:8]([CH3:10])[CH3:9].COC1C=C(C=CC=1OC)C=O.C(N)(C)C.[OH-].[Na+].[Cl:34][CH:35]([Cl:39])[C:36](Cl)=[O:37]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH2:6][N:7]([CH:8]([CH3:10])[CH3:9])[C:36](=[O:37])[CH:35]([Cl:39])[Cl:34]

Participants

7

Reactant 5

HCID 6363IsopropylamineHCID 6593Dichloroacetyl chlorideHCID 8419VeratraldehydeHCID 14798Sodium HydroxideHCID 775251Benzenemethanamine, 3,4-dimethoxy-N-(1-methylethyl)-

Product 1

HCID 19826633HCID 19826633, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 126 g N-(3,4-dimethoxybenzyl)-N-isopropyl amine (prepared by condensing 3,4-dimethoxybenzaldehyde and isopropylamine and hydrogenating the conversation product b.p. 77.5°-77.8°/0.03 mbar) and 250 ml of toluene is stirred in a 750 ml 4-neckflask until the amine is dissolved. Then 120 g of 20% sodium hydroxide is added thereto and the reaction-mixture is cooled in a CO2 /alcohol bath to a temperature of -10°/-15°. A mixture of 89 g of dichloroacetic acid chloride in 100 ml of toluene is then added dropwise while stirring to the cold reaction mixture. A white precipitate forms immediately. When everything is added, what takes about 11/2hours, the cooling bath is removed and the reaction mixtured is stirred until room temperature has been reached. Then it is poured into an ice-water mixture. The phases are separated and the water-phase is extracted with toluene. The organic layer is then washed twice with 1N hydrochloric acid and twice with water, dried and concentrated. There remain 176 g (91.7% of the theory) or a clear sticky oil with a refraction index of nD22 1.5495 which eventually crystallizes m.p. 69°-72°.

Workup

  1. dissolutionis dissolved
  2. temperaturethe reaction-mixture is cooled in a CO2 /alcohol bath to a temperature of -10°/-15°
  3. additionis then added dropwise
  4. additionWhen everything is added
  5. custom2hours
  6. customthe cooling bath is removed
  7. customthe reaction
  8. stirringmixtured is stirred until room temperature
  9. customThe phases are separated
  10. extractionthe water-phase is extracted with toluene
  11. washThe organic layer is then washed twice with 1N hydrochloric acid and twice with water
  12. customdried
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-d302d17e8b37452390648424bddf0587
Source dataset
uspto-grants-1990_01
Patent number
US04897109

Reaction notes

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