Dimethylcarbamoyl Chloride → HCID 118115070, compound

HRID 1050596Notes

Reaction equation

HRID 1050596 reaction equation
[NH2:1][C@@H:2]1[C@H:7]([CH3:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.CCN(C(C)C)C(C)C.[CH3:25][N:26]([CH3:30])[C:27](Cl)=[O:28]>C1COCC1.CCOC(C)=O>[CH3:25][N:26]([CH3:30])[C:27](=[O:28])[NH:1][C@@H:2]1[C@H:7]([CH3:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:3]1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 58303396HCID 58303396, compound

Product 1

HCID 118115070HCID 118115070, compoundYield 105.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Commercial (3R,4R)-tert-butyl 3-amino-4-methylpiperidine-1-carboxylate (427, 250 mg, 1.16 mmol) was dissolved in 10 mL dry THF. To it were added DIEA (610 μL, 3.50 mmol) and dimethylcarbamoyl chloride (214 μL, 2.32 mmol). The mixture was stirred at RT for 2 hours, diluted with 100 mL EtOAc, washed with water ×3, dried, concentrated, and subjected to silica flash column using 0 to 5% MeOh in DCM to isolate (3R,4R)-tert-butyl 3-(3,3-dimethylureido)-4-methylpiperidine-1-carboxylate (428, 350 mg) in quantitative yield as a white solid. It was treated with 15 mL commercial 4N HCkl in dioxane at RT for 40 min to yield 1,1-dimethyl-3-((3R,4R)-4-methylpiperidin-3-yl)urea hydrochloride (429).

Workup

  1. washwashed with water ×3
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e76044b3d7d044b58c7f84dca73807e7
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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