Sec-Butylamine → HCID 12764046, compound

HRID 1903751Notes

Reaction equation

HRID 1903751 reaction equation
[C:1]([C:3]1[CH:13]=[C:12]([NH:14][C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:11]=[CH:10][C:4]=1[O:5][CH2:6][CH:7]1[O:9][CH2:8]1)#[N:2].[CH:22]([NH2:26])([CH2:24][CH3:25])[CH3:23]>C(O)C.C(OCC)(=O)C>[C:1]([C:3]1[CH:13]=[C:12]([NH:14][C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:11]=[CH:10][C:4]=1[O:5][CH2:6][CH:7]([OH:9])[CH2:8][NH:26][CH:22]([CH2:24][CH3:25])[CH3:23])#[N:2]

Participants

5

Reactant 2

HCID 24874Sec-ButylamineHCID 12939818HCID 12939818, compound

Product 1

HCID 12764046HCID 12764046, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ten grams (0.035 mol) of 1-(2-cyano-4-n-hexanoylamino-phenoxy)-2,3-epoxypropane were dissolved in 100 ml of ethanol, 7.3 gm (0.1 mol) of sec.butylamine were added, and the mixture was refluxed for one hour. After the solvent was distilled off in vacuo, the residue was purified by column chromatography in the manner described in Example 6. The base thus obtained was dissolved in ethyl acetate, washed with dilute NaOH and water, dried, and evaporated to dryness. The test substance remaining was recrystallized from ethyl acetate with the addition of petroleum ether. Subsequent recrystallization from acetonitrile yielded 2.4 gm of pure white crystalline base. M.p.: 72°-74° C.

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. distillationAfter the solvent was distilled off in vacuo
  3. customthe residue was purified by column chromatography in the manner
  4. customThe base thus obtained
  5. washwashed with dilute NaOH and water
  6. customdried
  7. customevaporated to dryness
  8. customThe test substance remaining was recrystallized from ethyl acetate with the addition of petroleum ether
  9. customSubsequent recrystallization from acetonitrile

Sources & evidence

ORD record
ord-10c37181157040f6ae13a7971b958a10
Source dataset
uspto-grants-1984_03
Patent number
US04438143

Reaction notes

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