N-(2-aminoethyl)acetamide → HCID 19593902, compound

HRID 1584540Notes

Reaction equation

HRID 1584540 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[S:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](OC)=[S:13].[NH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21]>O>[C:20]([NH:19][CH2:18][CH2:17][NH:16][C:12](=[S:13])[CH2:11][CH2:10][CH2:9][CH2:8][S:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 54516579HCID 54516579, compound

Product 1

HCID 19593902HCID 19593902, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Methyl [3-(tetrahydropyran-2-ylthio)propyl]thioacetate (1 g, 3.7 mmol) was added dropwise to N-(2-aminoethyl)-acetamide (1.25 g, 12.25 mmol) and the mixture heated at 75° C. for 2.5 h. Volatile components were then removed under reduced pressure (45° C. at 0.02 mmHg) to give an oil which was taken up into water. This aqueous solution was then extracted with dichloromethane (adding potassium chloride to the aqueous layer to prevent emulsion formation if necessary). The dichloromethane extracts were then dried (MgSO4), filtered, and the solvent removed under reduced pressure to give the crude N-(2-acetylaminoethyl)-3-(tetrahydropyran-2-ylthio)propylthioacetamide. A pure sample of this material (0.25 g, 22%) was obtained by reverse phase h.p.l.c. using aqueous methanol as the eluant.

Workup

  1. customVolatile components were then removed under reduced pressure (45° C. at 0.02 mmHg)
  2. customto give an oil which
  3. extractionThis aqueous solution was then extracted with dichloromethane (
  4. additionadding potassium chloride to the aqueous layer
  5. dry with materialThe dichloromethane extracts were then dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a33e79a7d40646a5a7631f873c5a1242
Source dataset
uspto-grants-1999_08
Patent number
US05932707

Reaction notes

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