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Ethanamine, 2,2,2-trifluoro- → Tert-butyl 4-((2,2,2-trifluoroethylamino)methyl)piperidine-1-carboxylate

HRID 518721
Notes
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Reaction equation

HRID 518721 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=O.[F:16][C:17]([F:21])([F:20])[CH2:18][NH2:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl.C([O-])(O)=O.[Na+].CC(O)=O>[F:16][C:17]([F:21])([F:20])[CH2:18][NH:19][CH2:1][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 14798Sodium HydroxideHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66728665Tert-butyl 4-((2,2,2-trifluoroethylamino)methyl)piperidine-1-carboxylateYield 107.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent
HCID 6344DichloromethaneSolvent2×
HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl 4-formylpiperidine-1-carboxylate (1 g, 4.69 mmol) in DCM (25 mL) was added 2,2,2-trifluoroethanamine (0.464 g, 4.69 mmol) and AcOH (0.05 mL). The reaction was stirred at RT for 3 hours and then sodium triacetoxyborohydride (1.292 g, 6.10 mmol) was added, and the reaction was stirred at RT for 16 hours. The reaction was diluted with DCM and saturated aqueous NaHCO3. The aqueous layer was adjusted to a pH of approximately 10 with 1 N aqueous NaOH, and extracted with DCM. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated to generate tert-butyl 4-((2,2,2-trifluoroethylamino)methyl)piperidine-1-carboxylate as a colorless oil (1.49 g, 107% yield).

Workup

  1. stirringthe reaction was stirred at RT for 16 hours
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-132d89b35c4d4591bbd4e4fc978306db
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115127B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes