Sodium Hydroxide → HCID 58138257, compound

HRID 1967561Notes

Reaction equation

HRID 1967561 reaction equation
[CH3:1][C:2]([NH:14]C(=O)C)([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[N:5]=1)[CH3:3].[OH-].[Na+]>Cl>[CH3:3][C:2]([NH2:14])([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([F:11])([F:13])[F:12])[N:5]=1)[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66919737HCID 66919737, compound

Product 1

HCID 58138257HCID 58138257, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Heat a solution of N-[1-methyl-1-(2-trifluoromethyl-pyrimidin-4-yl)-ethyl]-acetamide (15.4 g, 62 mmol) and aqueous 5N HCl (150 mL) to 100° C. for 20 hours then cool to room temperature. Extract the reaction with diethyl ether (2×) then make the aqueous layer alkaline with aqueous 5N NaOH. Extract the aqueous layer with diethyl ether (3×), dry the combined organic layers over sodium sulfate, filter, and concentrate under reduced pressure to give 1-methyl-1-(2-trifluoromethyl-pyrimidin-4-yl)-ethylamine (7.2 g, 56%) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 8.80 (d, J=5.3 Hz, 1H), 7.68 (d, J=5.3 Hz, 1H), 1.76 (br s, 2H), 1.49 (s, 6H).

Workup

  1. extractionExtract
  2. customthe reaction with diethyl ether (2×)
  3. extractionExtract the aqueous layer with diethyl ether (3×)
  4. dry with materialdry the combined organic layers over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-ba8723eee2c64605a41d0af368d96712
Source dataset
uspto-grants-2013_04
Patent number
US08420654B2

Reaction notes

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