Triethylamine → HCID 14155738, compound

HRID 1252153Notes

Reaction equation

HRID 1252153 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:6][CH:7]=O)[CH2:3][CH:4]=O.Cl.[NH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:9])[CH:6]=[CH:7][N:11]([CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:4]=[CH:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27563834-Aminobutyric acid methyl ester hydrochlorideHCID 11116082HCID 11116082, compound

Product 1

HCID 14155738HCID 14155738, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under nitrogen, 5.89 g (0.046 mole) of 3,3-dimethylglutaraldehyde, 7.03 g (0.0457 mole) of methyl 4-aminobutanoate hydrochloride (the compound of Example 9a), and 9 g of 5A molecular sieves were combined in 425 ml of chloroform at room temperature. 7.0 ml (0.05 mole) of triethylamine were added to the reaction mixture before it was warmed to reflux. After 21 hours the reaction mixture was cooled to room temperature, filtered, and the filtrate evaporated in vacuo. The residue was suspended in about 300 ml of ethyl ether and filtered. The filtrate was evaporated in vacuo to yield 8.56 g of crude product. The crude product was distilled to yield 2.5 g of the title compound as a clear liquid, bp 95° C./0.2 mm Hg.

Workup

  1. temperaturewas warmed to reflux
  2. filtrationfiltered
  3. customthe filtrate evaporated in vacuo
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customto yield 8.56 g of crude product
  7. distillationThe crude product was distilled

Sources & evidence

ORD record
ord-3392d5cb897f4c1a950e3fed2eb4240c
Source dataset
uspto-grants-1988_05
Patent number
US04742068

Reaction notes

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