Hydrochloric Acid → HCID 59718885, compound

HRID 383533Notes

Reaction equation

HRID 383533 reaction equation
Cl.[C:2]1(=O)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:11]([NH2:15])[CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[Na+].[Na+].[CH3:22][O:23][C:24]([CH:26]([C:31](OC)=[O:32])[C:27](OC)=[O:28])=[O:25]>C(OCC)(=O)C>[CH2:11]([N:15]1[C:27](=[O:28])[C:26]([C:24]([O:23][CH3:22])=[O:25])=[C:31]([OH:32])[C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:2]1=2)[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8007ButylamineHCID 10340Sodium CarbonateHCID 10403CyclooctanoneHCID 136922Trimethyl methanetricarboxylate

Product 1

HCID 59718885HCID 59718885, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A concentrated hydrochloric acid was added to a mixture of cyclooctanone (3.84 g, 30.43 mmol) and butylamine (3.01 mL, 30.43 mmol) by two drops, and the mixture was stirred at room temperature for 15 hours. Diluted sodium carbonate aqueous solution and ethyl acetate were added in the reaction mixture to separate the mixture, and the organic layer was washed with water and saturated saline. After the organic layer had been dried, the solvent was removed by distillation and 4.72 g of colorless oily matter was obtained (86%). This imine (4.67 g, 25.76 mmol) was reacted as mentioned above together with trimethylmethane tricarboxylic acid (3.42 g, 18 mM) in trigrim (40 mL), and viscous yellow oily matter (AA17, 2.62 g, 47%) was obtained.

Workup

  1. customto separate the mixture
  2. washthe organic layer was washed with water and saturated saline
  3. customAfter the organic layer had been dried
  4. customthe solvent was removed by distillation and 4.72 g of colorless oily matter
  5. customwas obtained (86%)
  6. customwas obtained

Sources & evidence

ORD record
ord-8c0f7b9bbb6049108bf3d5d4a71474e0
Source dataset
uspto-grants-2013_02
Patent number
US08367666B2

Reaction notes

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