2-Dimethylaminopyridine → HCID 178520426, compound

HRID 129536

Reaction equation

HRID 129536 reaction equation
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].CN(C1C=CC=CN=1)C.[CH:17]1([CH2:23][CH2:24][C:25](O)=[O:26])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.Cl.CN(C)CCCN=C=NCC.[K+].[Br-]>CN(C)C=O.C(N(CC)CC)C>[CH:17]1([CH2:23][CH2:24][C:25]([C:1]2[C:6](=[O:7])[O:5][CH2:4][C:2]=2[OH:3])=[O:26])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

8

Reactant 5

HCID 218852-DimethylaminopyridineHCID 69702Cyclohexanepropanoic acidHCID 253877Potassium BromideHCID 521261Tetronic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 178520426HCID 178520426, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2.0 g of tetronic acid in 40 ml of dry N,N-dimethylformamide was added (at 0° C.) 3.1 ml of triethylamine and 0.81 g of dimethylaminopyridine. After stirring for 5 minutes, 3.4 ml of 3-cyclohexylpropanoic acid was added, followed by 4.6 g of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride. After 10 minutes the ice bath is removed and the mixture is allowed to stir overnight. The reaction mixture is quenched with 1N hydrochloric acid and the solution is washed 3 times with hexanes. The combined organic layers are combined, washed with brine, dried over magnesium sulfate and evaporated to give a yellow solid, which is recrystallized from hexanes to give light yellow crystals: m.p. 75°-78° C.; IR (KBr) 2910, 2820, 1750, 1640, 1600 cm-1 ; NMR (CDCl3) δ 0.9-1.8 (1 1H, m), 2.9 (t, 2H, J=6 Hz), 4.7 and 4.5 (s, 2H (tautomers)); MS EI M+ 238.

Workup

  1. customAfter 10 minutes the ice bath is removed
  2. stirringto stir overnight
  3. customThe reaction mixture is quenched with 1N hydrochloric acid
  4. washthe solution is washed 3 times with hexanes
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customto give a yellow solid, which
  9. customis recrystallized from hexanes
  10. customto give light yellow crystals

Sources & evidence

ORD record
ord-1b443bad3e6b46e5ab539d1cb4d0abec
Source dataset
uspto-grants-1995_11
Patent number
US05468774

Linked notes

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