Diethyl Ether → HCID 1415664, compound

HRID 615103Notes

Reaction equation

HRID 615103 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[C:6](=O)([O-])[O-].[K+].[K+].CCO[CH2:15][CH3:16].[CH2:17](Br)[C:18]#[CH:19]>O>[CH2:17]([N:5]([CH2:6][C:15]#[CH:16])[C:1]([CH3:4])([CH3:3])[CH3:2])[C:18]#[CH:19]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6385Tert-ButylamineHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 1415664HCID 1415664, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.15 mole of t-butylamine, 0.35 mole of anhydrous, powdered potassium carbonate and 250 moles of ether was stirred mechanically and 0.25 mole of propargylbromide was added dropwise. The mixture was refluxed for about 10 hours. Water was added to dissolve the salt. The ether layer was separated and the aqueous layer was extracted twice with ether. The combined ether solution was dried over anhydrous MgSO4. The dipropargyl-t-butylamine produced was distilled at 63°-65° C./20 mm Hg to yield a yellowish liquid in a 45% yield: IR 3300, 3100, 2980 and 2940 cm-1 ; NMR (CDCl3)δ1.10, 2.20 and 3.45.

Workup

  1. temperatureThe mixture was refluxed for about 10 hours
  2. dissolutionto dissolve the salt
  3. customThe ether layer was separated
  4. extractionthe aqueous layer was extracted twice with ether
  5. dry with materialThe combined ether solution was dried over anhydrous MgSO4

Sources & evidence

ORD record
ord-619fe9d62bc942ba8196281b4b06560f
Source dataset
uspto-grants-1985_02
Patent number
US04497727

Reaction notes

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