Diisobutylamine → HCID 13558652, compound

HRID 1534574Notes

Reaction equation

HRID 1534574 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:10]([NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH:11]([CH3:13])[CH3:12]>[I-].[Na+].C1(C)C(C)=CC=CC=1>[CH2:10]([N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 8085DiisobutylamineHCID 18474Ethyl 4-chlorobutyrate

Product 1

HCID 13558652HCID 13558652, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 7237O-XyleneSolvent

Procedure

To 180 ml of xylene were added 176 grams of ethyl gamma-chlorobutyrate, 302.2 grams of diisobutylamine and 6.0 grams of sodium iodide and the mixture was heated to reflux on an oil bath of 120° to 140° C. for 62 hours. After cooling, salts separated out therefrom were removed by filtration, the filtrate was washed with ether, concentrated, and the residue was distilled in vacuo to give 112 grams of the colorless oily product, b.p. 102-6° C./2 mmHg.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux on an oil bath of 120° to 140° C. for 62 hours
  3. temperatureAfter cooling
  4. customsalts separated out
  5. customtherefrom were removed by filtration
  6. washthe filtrate was washed with ether
  7. concentrationconcentrated
  8. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-3b9415c232f543bf947587f89e207989
Source dataset
uspto-grants-1992_02
Patent number
US05089529

Reaction notes

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