Phenethylamine → HCID 22467126, compound

HRID 1934772Notes

Reaction equation

HRID 1934772 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH2:23])=[CH:17][CH:16]=1.[SH:24][CH:25]([CH2:29][C:30]([OH:32])=[O:31])[C:26](O)=[O:27].C(OCC)(=O)C>C1(C)C=CC=CC=1>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][C:2]2([S:24][CH:25]([CH2:29][C:30]([OH:32])=[O:31])[C:26](=[O:27])[N:23]2[CH2:22][CH2:21][C:18]2[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=2)[CH2:3][CH2:4]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 6268(+-)-Mercaptosuccinic acidHCID 8857Ethyl AcetateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 22467126HCID 22467126, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 200 ml of toluene were dissolved 20.00 g of tert-butyl 4-oxo-1-piperidinecarboxylate and 12.6 ml of β-phenethylamine. After stirring the resulting solution at ambient temperature for 30 minutes, 15.07 g of mercaptosuccinic acid was added, and the resulting mixture was subjected to an azeotropic distillation treatment under reflux for 6 hours. The reaction mixture was poured into a mixture of ice water and ethyl acetate, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by column chromatography [eluent: toluene:ethyl acetate=5:1] gave 22.10 g of 2-[8-(tert-butoxycarbonyl)-3-oxo-4-phenethyl-1-thia-4,8-diazaspiro[4.5]decan-2-yl]-acetic acid as a yellow oily product.

Workup

  1. temperatureunder reflux for 6 hours
  2. customthe organic layer was separated
  3. washThe organic layer was washed successively with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customPurification of the residue by column chromatography [eluent: toluene:ethyl acetate=5:1]

Sources & evidence

ORD record
ord-6a8d5eb79c014442a35b31f85c293275
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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