Hydrochloric Acid → HCID 20080118, compound

HRID 1654283Notes

Reaction equation

HRID 1654283 reaction equation
Cl.[CH2:2]([NH2:4])[CH3:3].C[Al](C)C.[OH:9][CH:10]([CH3:18])[CH2:11][CH2:12][CH2:13][CH2:14][C:15](O)=[O:16].Cl>C1(C)C=CC=CC=1.CCCCCC>[CH2:2]([NH:4][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([OH:9])[CH3:18])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11198Ethylamine hydrochlorideHCID 5312788HCID 5312788, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 20080118HCID 20080118, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of dry ethylamine hydrochloride (3.26 g, 0.04 mol) in toluene, under nitrogen, was cooled in an ice bath and treated during 40 minutes with 20 ml of a 2.0M solution of trimethylaluminum in hexane. The mixture was kept at 0° for 10 minutes and at ambient temperature for 2.5 hours. A portion of the resulting solution (46.8 ml) was added, under nitrogen, during 15 minutes to a solution of the product from Step I (2.0 g, 0.016 mol) in toluene (100 ml). This mixture was warmed at 80° C. for 3 hours, cooled and added continuously to dilute HCl. The product was extracted with ethyl acetate. The extracts were dried (MgSO4) and concentrated to give 2.27 g of N-ethyl-6-hydroxyheptanamide.

Workup

  1. temperatureunder nitrogen, was cooled in an ice bath
  2. temperaturecooled
  3. extractionThe product was extracted with ethyl acetate
  4. dry with materialThe extracts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9584d28a128f4aaab03e21719721b860
Source dataset
uspto-grants-1995_04
Patent number
US05405997

Reaction notes

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