Ethylamine → HCID 13137236, compound

HRID 978608Notes

Reaction equation

HRID 978608 reaction equation
[CH2:1]([NH2:3])[CH3:2].[CH2:4]([CH:9]1[C:13](O)([CH3:14])[CH:12]=[CH:11][C:10]1=[O:16])[CH2:5][CH2:6][CH2:7][CH3:8]>O1CCCC1>[CH2:4]([C:9]1[C:10](=[O:16])[CH2:11][CH:12]([NH:3][CH2:1][CH3:2])[C:13]=1[CH3:14])[CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 13137234HCID 13137234, compound

Product 1

HCID 13137236HCID 13137236, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a four-necked flask equipped with a stirrer and a thermometer, a 30% aqueous solution of monoethylamine (70 g) and tetrahydrofuran (18 g) were charged, and then 2-n-pentyl-3-hydroxy-3-methyl-4-cyclopentenone (18.2 g) was dropwise added thereto at a temperature of 10° to 20° C. for 30 minutes. At the same temperature, the reaction mixture was kept for 2 hours. After completion of the reaction, the mixture was extracted with toluene, and the organic layer was washed with water. From the organic layer, toluene was evaporated off to give 2-n-pentyl-3-methyl-4-ethylamino-2-cyclopentenone (20.3 g). Yeild, 97%. The product was purified by alumina chromatography using toluene-ethyl acetate (10:1 by volume). nD20 1.4864.

Workup

  1. customInto a four-necked flask equipped with a stirrer
  2. waitAt the same temperature, the reaction mixture was kept for 2 hours
  3. customAfter completion of the reaction
  4. extractionthe mixture was extracted with toluene
  5. washthe organic layer was washed with water
  6. customFrom the organic layer, toluene was evaporated off

Sources & evidence

ORD record
ord-e92a4b6c6f7e4f44b0a80d39ae35877c
Source dataset
uspto-grants-1987_05
Patent number
US04665174

Reaction notes

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