Water → HCID 67169151, compound

HRID 872673Notes

Reaction equation

HRID 872673 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[O:8][CH:7]=1)=[O:5].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>C(Cl)Cl>[CH3:24][S:25]([N:14]1[CH2:15][CH2:16][CH:11]([C:9]2[O:8][CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[N:10]=2)[CH2:12][CH2:13]1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 40429419Ethyl 2-(piperidin-4-yl)-1,3-oxazole-4-carboxylate

Product 1

HCID 67169151HCID 67169151, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-(4-piperidino)-1,3-oxazole-4-carboxylate (500 mg, 2.230 mmol) and triethylamine (0.466 ml, 3.34 mmol) were dissolved in dry DCM and cooled down to 0° C. Methanesulfonyl chloride (0.190 ml, 2.453 mmol) was added slowly at 0° C. and the reaction mixture was stirred at RT overnight. Small amount of water was added carefully and organic phase was washed with 1M Na2CO3 and water. Organic phase was dried and evaporated to yield the title compound 89%. 1H-NMR (400 MHz; CDCl3): δ 1.38 (t, 3H), 1.97-2.11 (m, 2H), 2.15-2.24 (m, 2H), 2.81 (s, 3H), 2.88-3.07 (m, 3H), 3.72-3.82 (m, 2H), 4.39 (q, 2H), 8.17 (s, 1H).

Workup

  1. washorganic phase was washed with 1M Na2CO3 and water
  2. customOrganic phase was dried
  3. customevaporated

Sources & evidence

ORD record
ord-c5ec5638dc7949a3b455064aee2e2db5
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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