Triethylamine → HCID 20367044, compound

HRID 616977Notes

Reaction equation

HRID 616977 reaction equation
C(N(CC)CC)C.[Cl-].[CH2:9]([O:11][C:12]1([NH3+:15])[CH2:14][CH2:13]1)[CH3:10].[C:16](Cl)(=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>O1CCCC1>[CH2:9]([O:11][C:12]1([NH:15][C:16](=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:13]1)[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67340Hexanoyl chlorideHCID 20367034HCID 20367034, compound

Product 1

HCID 20367044HCID 20367044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (2.22 g, 22 mmol) is added dropwise (15 min) with vigorous stirring at 0° to a solution of 1-ethoxycyclopropylammonium chloride (1.37 g, 10 mmol) and caproyl chloride (1.34 g, 10 mmol) in dry tetrahydrofuran (30 ml) and the mixture is stirred at room temperature for 1 hr. The precipitate is filtered off and the filtrate is evaporated in vacuo. The crystalline residue (1.85 g) is dissolved in petroleum ether (20 ml) and the solution is filtered through a short silica-gel column (2 cm × 10 cm). After evaporation the residue (1.30 g) is recrystallised from petroleum ether (at low temperature) yielding pure N-(1-ethoxycyclopropyl)-caproic amide, mp 47°-48.5° (1.0 g, 50%); NMR (60 MHz): δCDCl 3 = 0.7-1.9 (m, 16H), 2.0-2.4 and 2.4-2.8 (2 m, total 2H), 3,57 and 3.63 (2q, J=7.2 Hz, total 2H), 6.7 (br. s, 1H), (two rotamers).

Workup

  1. filtrationThe precipitate is filtered off
  2. customthe filtrate is evaporated in vacuo
  3. dissolutionThe crystalline residue (1.85 g) is dissolved in petroleum ether (20 ml)
  4. filtrationthe solution is filtered through a short silica-gel column (2 cm × 10 cm)
  5. customAfter evaporation the residue (1.30 g)
  6. customis recrystallised from petroleum ether (at low temperature)

Sources & evidence

ORD record
ord-2db1fd94296544b6821d0c3633512029
Source dataset
uspto-grants-1978_02
Patent number
US04076840

Reaction notes

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