Ethanolamine → 2-[4-(5-Bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]amino ethanol

HRID 1748616Notes

Reaction equation

HRID 1748616 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:15])[C:5]([C:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH:9]=2)=[N:6][CH:7]=1.[NH2:16][CH2:17][CH2:18][OH:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH3:15])[C:5]([C:8]2[CH2:13][CH2:12][CH:11]([NH:16][CH2:17][CH2:18][OH:19])[CH2:10][CH:9]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 866925604-(5-Bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-one

Product 1

HCID 866925612-[4-(5-Bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]amino ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-one (2.06 g) in dichloromethane (50 ml) was added 2-aminoethanol (0.463 ml) at room temperature with stirring. Then sodium triacetoxyborohydride (1.64 g) was added thereto, and stirred at the same temperature. After completion of the reaction, to the reaction solution was added 10% sodium carbonate aqueous solution, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (chloroform/methanol), and then suspended and washed with a mixed solvent of a small amount of diethyl ether and n-hexane to give 2-[4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]amino ethanol (860 mg) as a light brown solid.

Workup

  1. stirringstirred at the same temperature
  2. customAfter completion of the reaction
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified with silica gel column chromatography (chloroform/methanol)
  7. washwashed with a mixed solvent of a small amount of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-70f0fc8b3ba141899067693b07595703
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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