Propargyl bromide → HCID 15065591, compound

HRID 846649Notes

Reaction equation

HRID 846649 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[CH2:5]([O:7][CH:8]([O:11][CH2:12][CH3:13])[CH2:9][NH2:10])[CH3:6].[CH2:14]1[CH2:18]OC[CH2:15]1>>[CH2:5]([O:7][CH:8]([O:11][CH2:12][CH3:13])[CH2:9][N:10]([CH2:18][C:14]#[CH:15])[CH2:1][C:2]#[CH:3])[CH3:6].[CH2:5]([O:7][CH:8]([O:11][CH2:12][CH3:13])[CH2:9][NH:10][CH2:1][C:2]#[CH:3])[CH3:6]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8028TetrahydrofuranHCID 695242,2-Diethoxyethylamine

Product 2

HCID 15065591HCID 15065591, compoundHCID 15065592HCID 15065592, compound

Procedure

Propargyl bromide (14.7 g of 80% solution in toluene, 0.1 mol) was added to a stirred solution of aminoacetaldehyde diethyl acetal (13.3 g, 0.1 mol) in THF (200 mL). After 2 h the THF was removed and the residual oil was partitioned between ether and sodium hydroxide solution. Evaporation of the ether gave an oil which was chromatographed on silica gel to give 4.7 g of 2,2-diethoxy-N,N-bis-(2-propynyl)ethylamine and 8.1 g of 2,2-diethoxy-N-(2-propynyl)ethylamine.

Workup

  1. customAfter 2 h the THF was removed
  2. customthe residual oil was partitioned between ether and sodium hydroxide solution
  3. customEvaporation of the ether
  4. customgave an oil which
  5. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-3b138228e9f642d28b60a09a16aeb651
Source dataset
uspto-grants-1992_08
Patent number
US05137905

Reaction notes

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