Sodium Hydroxide → HCID 189201, compound

HRID 1906426Notes

Reaction equation

HRID 1906426 reaction equation
FC(F)(F)C([NH:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.[OH-].[Na+]>CO>[C:13]1([CH:12]=[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]2[NH2:5])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54503179HCID 54503179, compound

Product 1

HCID 189201HCID 189201, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.4 g (5 mmole) of the 2,2,2-trifluoro-N-[2-(phenylmethylene)cyclohexy]acetamide, Z isomer from step (c) above, 7 ml of 20% w/v aqueous sodium hydroxide solution and 7 ml of methanol was heated on a steam bath for 5 min. The methanol was evaporated and the residue was extracted with diethyl ether. The ether extract was washed with saturated sodium chloride solution, dried with magnesium sulfate and evaporated to leave 0.94 g of the N-[2-(phenylmethylene)cyclohexyl]amine, Z isomer, as a colorless oil. The NMR spectrum was consistent; the CH--N coupling pattern suggests that this H is equatorial. The GC analysis, 1% QF-1, 99.7%, retention time 2.36 min UV λmax(ε)243(12,000). The mass spectrum and IR were also consistent. The hydrochloride salt of this amine was formed in ethereal hydrogen chloride and crystallized from a methanol/diethyl ether mixture, mp 214°-215° C. The mass spectrum and IR spectrum were consistent with this sub-titled hydrochloride salt.

Workup

  1. temperaturewas heated on a steam bath for 5 min
  2. customThe methanol was evaporated
  3. extractionthe residue was extracted with diethyl ether
  4. extractionThe ether extract
  5. washwas washed with saturated sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-88e76897512646c9b846f523f387f038
Source dataset
uspto-grants-1987_03
Patent number
US04652559

Reaction notes

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