Hydrochloric Acid → HCID 66732179, compound

HRID 1963234Notes

Reaction equation

HRID 1963234 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][N:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:3])[NH2:2].[ClH:15]>CO.[Pt](=O)=O>[ClH:15].[C:1]([CH:4]1[CH2:5][CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:12][CH2:13][NH:14]1)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11790073Ethyl 2-carbamoylisonicotinate

Product 1

HCID 66732179HCID 66732179, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst3×HCID 887MethanolSolvent2×

Procedure

Ethyl 2-carbamoylisonicotinate (4.24 g, 21.83 mmol) was slurried in MeOH (50 mL) and HCl in MeOH (17.47 mL, 21.83 mmol) and platinum(IV) oxide (0.248 g, 1.09 mmol) were added. The mixture was hydrogenated at 5 bar in a Büchi hydrogenation apparatus. After 3 h there were still starting material left. platinum(IV) oxide (0.14 g, 0.62 mmol) was added and the reaction continued for 2 h when platinum(IV) oxide (0.387 g, 1.70 mmol) was added and the reaction was stirred overnight. The reaction mixture was filtered and evaporated to give ethyl 2-carbamoylpiperidine-4-carboxylate hydrochloride (3.93 g, 90%). 1H NMR (400 MHz, dmso) δ 1.16 (t, 3H), 1.31-1.63 (m, 2H), 1.86 (d, 1H), 2.26 (d, 1H), 2.54-2.66 (m, 1H), 2.74-2.88 (m, 1H), 3.10-3.19 (m, 1H), 3.47-3.56 (m, 1H), 4.06 (q, 2H), 7.38 (s, 1H), 7.71 (s, 1H). MS m/z 201 (M+H)+

Workup

  1. waitmaterial left
  2. waitthe reaction continued for 2 h
  3. filtrationThe reaction mixture was filtered
  4. customevaporated

Sources & evidence

ORD record
ord-684d76cec9e149878a2c588733a223e8
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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