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Trifluoroacetic acid → 2,2,2-Trifluoro-1-[7-(phenylmethyl)-4,7-diazaspiro[2.5]oct-4-yl]ethanone

HRID 421422
Notes
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Reaction equation

HRID 421422 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](O)=[O:4].[CH2:8]([N:15]1[CH2:22][C:19]2([CH2:21][CH2:20]2)[NH:18][CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[CH2:8]([N:15]1[CH2:22][C:19]2([CH2:21][CH2:20]2)[N:18]([C:3](=[O:4])[C:2]([F:7])([F:6])[F:1])[CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 585423257-Benzyl-4,7-diazaspiro[2.5]octane

Product 1

HCID 585424062,2,2-Trifluoro-1-[7-(phenylmethyl)-4,7-diazaspiro[2.5]oct-4-yl]ethanoneYield 102.1%

Reagents, catalysts & solvents 2

HCID 6212
Chloroform
Solvent
HCID 6344DichloromethaneSolvent

Procedure

Anhydrous trifluoroacetic acid (8.50 ml, 61.1 mmol) was added dropwise to a methylene chloride (200 ml) solution of the compound (10.3 g, 50.9 mmol) obtained in Step 3 above and triethylamine (17 ml, 122 mmol) with ice cooling and the resulting mixture was stirred at the same temperature for 1 hour. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture, the resulting mixture was diluted with chloroform, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (15.5 g, 100%) as a colorless oil.

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-90054477dd8743009b7578dece06e185
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08097622B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes