Propylamine → N-n-Propyl-4-[(E)-2-(4,4-dimethyl-6-chromanyl)-2-methylvinyl]benzamide

HRID 1382906Notes

Reaction equation

HRID 1382906 reaction equation
[CH3:1][C:2]1([CH3:24])[C:11]2[C:6](=[CH:7][CH:8]=[C:9](/[C:12](/[CH3:23])=[CH:13]/[C:14]3[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=3)[CH:10]=2)[O:5][CH2:4][CH2:3]1.[CH2:25]([NH2:28])[CH2:26][CH3:27]>C(Cl)(Cl)Cl.C(OCC)C.[OH-].[Na+]>[CH2:25]([NH:28][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14](/[CH:13]=[C:12](/[C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[O:5][CH2:4][CH2:3][C:2]3([CH3:24])[CH3:1])\[CH3:23])=[CH:15][CH:16]=1)[CH2:26][CH3:27]

Participants

6

Reactant 2

HCID 7852PropylamineHCID 6366138(E)-p-(2-(4,4-Dimethylchroman-6-yl)propenyl)benzoic acid

Product 1

HCID 14372182N-n-Propyl-4-[(E)-2-(4,4-dimethyl-6-chromanyl)-2-methylvinyl]benzamide

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A 15 ml aliquot of the chloroform solution of the mixed anhydride of 4-[(E)-2-(4,4-dimethyl-6-chromanyl)-2-methylvinyl]benzoic acid from Preparation 13 was added to a solution of 0.1 g (1.71 mmole) of n-propylamine in ca. 25 ml of chloroform at 0° C. The reaction mixture was filtered and then it was extracted twice with 1N hydrochloric acid. The resulting chloroform solution was dried (MgSO4) and evaporated in vacuo to give an oily solid. This solid was dissolved in diethyl ether and 2N sodium hydroxide. The layers were separated and the ether layer was filtered, dried (MgSO4) and evaporated in vacuo. The residue was recrystallized from diethyl ether-hexane, to give 0.127 g of the title compound, mp 138°-139° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionit was extracted twice with 1N hydrochloric acid
  3. dry with materialThe resulting chloroform solution was dried (MgSO4)
  4. customevaporated in vacuo
  5. customto give an oily solid
  6. customThe layers were separated
  7. filtrationthe ether layer was filtered
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo
  10. customThe residue was recrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-20130e54c08147d0bb451d23771f5197
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Reaction notes

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