2450-71-7 → HCID 19033955, compound

HRID 1720127Notes

Reaction equation

HRID 1720127 reaction equation
[C:1]([NH2:4])#[C:2][CH3:3].[C:5](Cl)(=[O:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>C(N(CC)CC)C>[C:1]([NH:4][C:5](=[O:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])#[C:2][CH3:3]

Participants

4

Reactant 2

HCID 171402450-71-7HCID 69819Nonanoyl chloride

Product 1

HCID 19033955HCID 19033955, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

Propynylamine (10.4 ml, 151.2 mmol) was mixed with 150 ml of triethylamine in a round bottom flask immersed in a cold water bath, and vigorously stirred while nonanoyl chloride (27.0 ml, 149.75 retool) was added in portions from a dropping funnel over a 30 minute period. Additional triethylamine (100 ml) was added to facilitate stirring. At the end of the addition, the water bath was removed and the reaction was stirred for 30 minutes, then filtered. The filtrate was stripped down to a yellow solid. The solid was partitioned between ether and aqueous NaOH, requiring a considerable quantity of ether to dissolve. The combined ether extracts were stripped and recrystallized from heptane to give product as a white crystalline solid, 18.12 g, 92.8 mmol, 62% yield; top. 78°-79.5° C.; 1H NMR (CDCl3) ∂0.88 (t, J=6.0 Hz, 3 H), 1.28 (m, 10 H), 1.63 (m, 2 H), 2.19 (t, J= 7.6 Hz, 2 H), 2.22 (t, J=2.7 Hz, 1 H), 4.06 (dd, J=5.2, 2.6 Hz), 5.62 (br s, 1 H); EI mass spectrum m/z 196 (M+H)+.

Workup

  1. customimmersed in a cold water bath
  2. additionwas added in portions from a dropping funnel over a 30 minute period
  3. additionAt the end of the addition
  4. customthe water bath was removed
  5. stirringthe reaction was stirred for 30 minutes
  6. filtrationfiltered
  7. customThe solid was partitioned between ether and aqueous NaOH
  8. dissolutionto dissolve
  9. customrecrystallized from heptane
  10. customto give product as a white crystalline solid, 18.12 g, 92.8 mmol, 62% yield
  11. custom78°-79.5° C.

Sources & evidence

ORD record
ord-e040a745165b4eac9bcfc6f59f02f34c
Source dataset
uspto-grants-1996_04
Patent number
US05504237

Reaction notes

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