2,2,2-Trifluoroacetaldehyde hydrate → Benzyl 4-(2-(2,2,2-trifluoroethylidene)hydrazinyl)piperidine-1-carboxylate

HRID 2196550

Reaction equation

HRID 2196550 reaction equation
[NH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1)[NH2:2].O.[F:20][C:21]([F:25])([F:24])[CH:22]=O>CCO>[F:20][C:21]([F:25])([F:24])[CH:22]=[N:2][NH:1][CH:3]1[CH2:4][CH2:5][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 27813662,2,2-Trifluoroacetaldehyde hydrateHCID 21098319Benzyl 4-hydrazinylpiperidine-1-carboxylate

Product 1

HCID 69095121Benzyl 4-(2-(2,2,2-trifluoroethylidene)hydrazinyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 109 (4 g, 8.38 mmol) in EtOH (42 ml) was added trifluoroacetaldehyde hydrate (0.648 ml, 8.38 mmol) and the resulting solution was allowed to stir for 3 h at 70° C. The solvent was evaporated and AcOEt was added to the residue and the organic layer was washed with 1N HCl then with brine, dried over MgSO4, filtrated and concentrated. Crude 110 was obtained as yellow oil and was used as is for the next step. LRMS (ESI): calc. 329.3; found 330.2 (MH)+.

Workup

  1. customThe solvent was evaporated
  2. additionAcOEt was added to the residue
  3. washthe organic layer was washed with 1N HCl
  4. dry with materialwith brine, dried over MgSO4
  5. filtrationfiltrated
  6. concentrationconcentrated
  7. customCrude 110 was obtained as yellow oil

Sources & evidence

ORD record
ord-74240461c041455c8a447d271bdbd3e6
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Linked notes

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