Acetic Acid → 2-(1-(4-Bromothiazol-2-yl)piperidin-4-ylamino)ethanol

HRID 1401852Notes

Reaction equation

HRID 1401852 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([N:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[S:5][CH:6]=1.[NH2:14][CH2:15][CH2:16][OH:17].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C1COCC1.CC(=O)OCC.O>[Br:1][C:2]1[N:3]=[C:4]([N:7]2[CH2:12][CH2:11][CH:10]([NH:14][CH2:15][CH2:16][OH:17])[CH2:9][CH2:8]2)[S:5][CH:6]=1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 700EthanolamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 67323440HCID 67323440, compound

Product 1

HCID 673233402-(1-(4-Bromothiazol-2-yl)piperidin-4-ylamino)ethanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

100 mg (0.37 mmol) of 1-(4-bromothiazol-2-yl)piperidin-4-one from step a and 22 μl (0.37 mmol) of 2-aminoethanol were suspended in 7 ml of THF, stirred at room temperature for 1 h, 21 μl (0.37 mmol) of glacial acetic acid and 164 mg (0.74 mmol) of sodium triacetoxyborohydride were added. The mixture was stirred at room temperature overnight, water and EA were added, the mixture was adjusted to pH 12 using a concentrated NaOH solution and extracted by shaking with EA. The organic phase was dried over sodium sulfate, filtered and evaporated.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionextracted
  3. stirringby shaking with EA
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f694327016af4f8aa5401ac86b1c355a
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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