2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 66732449, compound

HRID 1963583Notes

Reaction equation

HRID 1963583 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[CH2:12][CH:11]([C:13]([OH:15])=O)[CH2:10][CH2:9][N:8]2[C:16]([O:18][CH3:19])=[O:17])=[CH:4][CH:3]=1.[CH3:22][C:23]1([CH3:31])[O:28][C:27](=[O:29])[CH2:26][C:25](=[O:30])[O:24]1.CCN(C(C)C)C(C)C.Cl.C(N=C=NCCCN(C)C)C>CN(C1C=CN=CC=1)C.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:12][CH:11]([C:13](=[C:26]3[C:27](=[O:29])[O:28][C:23]([CH3:31])([CH3:22])[O:24][C:25]3=[O:30])[OH:15])[CH2:10][CH2:9][N:8]2[C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66731865HCID 66731865, compound2×

Product 1

HCID 66732449HCID 66732449, compoundYield 117%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dichloromethane (200 mL) was added to 2-(4-chlorobenzyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (4.27 g, 13.7 mmol) (reference compound 51). The mixture was cooled with an ice bath. DMAP (2.008 g, 16.44 mmol), 2,2-dimethyl-1,3-dioxane-4,6-dione (2.96 g, 20.54 mmol) and DIPEA (5.25 mL, 30.13 mmol) were added and then N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (5.25 g, 27.39 mmol) was added. The mixture was stirred at 0° C. for 15 min, then the mixture was warmed to room temperature and stirred overnight. The organic phase was washed with 1 M HCl and once with water. The organic layer was filtered through a phase separator and evaporated to yield crude methyl 2-(4-chlorobenzyl)-4-((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)(hydroxy)methyl)-piperidine-1-carboxylate (7.00 g, 117%). MS m/z 438, 440 (M+H)+

Workup

  1. temperatureThe mixture was cooled with an ice bath
  2. temperaturethe mixture was warmed to room temperature
  3. stirringstirred overnight
  4. washThe organic phase was washed with 1 M HCl and once with water
  5. filtrationThe organic layer was filtered through a phase separator
  6. customevaporated

Sources & evidence

ORD record
ord-c74d4fb4633446bc9a24984c031a1847
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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