Isopropylamine → HCID 20466843, compound

HRID 1903749Notes

Reaction equation

HRID 1903749 reaction equation
[C:1]([C:3]1[C:14]([NH2:15])=[C:13]([C:16](=[O:24])[CH:17]([CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][CH:7]([OH:10])[CH2:8][Cl:9])#[N:2].[CH:25]([NH2:28])([CH3:27])[CH3:26]>C(O)C>[ClH:9].[C:1]([C:3]1[C:14]([NH2:15])=[C:13]([C:16](=[O:24])[CH:17]([CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][CH:7]([OH:10])[CH2:8][NH:28][CH:25]([CH3:27])[CH3:26])#[N:2]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 20466858HCID 20466858, compound

Product 1

HCID 20466843HCID 20466843, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Fifteen grams (0.043 mol) of 1-[2-cyano-4-(2-ethylhexanoyl)-amino-phenoxy]-3-chloro-2-propanol were dissolved in 80 ml of ethanol, 14.4 ml (0.17 mol) of isopropylamine were added, and the mixture was refluxed for two hours. The solvent was then distilled off, and the residue was purified on a silica gel column [mixture of eluants: ethyl acetate/isopropanol/NH4OH (14:6:1)]. The pure base obtained was recrystallized from ethyl acetate with the addition of petroleum ether. The crystals were dissolved in acetonitrile and acidified with alcoholic hydrochloric acid, and crystallization was initiated by the addition of ether. The crystals were pure white. Yield: 2.9 gm. M.p: 169°-170° C.

Workup

  1. temperaturethe mixture was refluxed for two hours
  2. distillationThe solvent was then distilled off
  3. customthe residue was purified on a silica gel column [mixture of eluants: ethyl acetate/isopropanol/NH4OH (14:6:1)]
  4. customThe pure base obtained
  5. customwas recrystallized from ethyl acetate with the addition of petroleum ether
  6. dissolutionThe crystals were dissolved in acetonitrile
  7. customacidified with alcoholic hydrochloric acid, and crystallization
  8. additionwas initiated by the addition of ether

Sources & evidence

ORD record
ord-205a5ef026214a81a95bb72b33b23717
Source dataset
uspto-grants-1984_03
Patent number
US04438143

Reaction notes

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