Sodium Hydroxide → 1,1-Dimethyl-2-[4-(2-methyl-thiazol-4-yl)-phenyl]-ethylamine

HRID 49387Notes

Reaction equation

HRID 49387 reaction equation
[CH3:1][C:2]([NH:17]C(=O)C(F)(F)F)([CH3:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([CH3:15])[S:13][CH:14]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO.O1CCCC1>[CH3:16][C:2]([NH2:17])([CH3:1])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([CH3:15])[S:13][CH:14]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18523660N-{1,1-Dimethyl-2-[4-(2-methyl-thiazol-4-yl)phenyl]-ethyl}-2,2,2-trifluoroacetamide

Product 1

HCID 205879471,1-Dimethyl-2-[4-(2-methyl-thiazol-4-yl)-phenyl]-ethylamineYield 93%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

In a round-bottomed flask, N-{1,1-dimethyl-2-[4-(2-methyl-thiazol-4-yl)-phenyl]-ethyl}-2,2,2-trifluoroacetamide (˜362 mg, 1.06 mmol) was suspended in 7.5 ml of 2:1 (v:v) methanol/tetrahydrofuran, and 5M sodium hydroxide (3.2 ml, 15 equiv.) was added dropwise. The solution turned from colorless to golden brown, and was then allowed to stir at room temperature overnight. The reaction mixture was then concentrated in vacuo to remove volatiles, and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqeuous layer was removed and was washed twice more with ethyl acetate. The combined organic extracts were then washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the product (242 mg, 93% yield for both steps), which was used directly without further purification. LRMS ([M+1]+)=247.3.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customto remove volatiles
  3. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. customThe aqeuous layer was removed
  5. washwas washed twice more with ethyl acetate
  6. washThe combined organic extracts were then washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto afford the product (242 mg, 93% yield for both steps), which
  11. customwas used directly without further purification

Sources & evidence

ORD record
ord-ec778f1054ae40f3a30d946d77244550
Source dataset
uspto-grants-2004_03
Patent number
US06706743B2

Reaction notes

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