Potassium Carbonate → HCID 178497928, compound

HRID 1814639Notes

Reaction equation

HRID 1814639 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[NH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.O>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][C:3]([CH2:2][NH:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]2)=[CH:4][CH:5]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 178511715HCID 178511715, compound

Product 1

HCID 178497928HCID 178497928, compoundYield 43.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 4-(bromomethyl)benzoate (5.0 g, 22 mmol) was dissolved in DMF (50 mL) and trans-4-aminocyclohexanol (3.04 g, 26 mmol) was added followed by addition of potassium carbonate (6.08 g, 44 mmol). The reaction mixture was heated to 80° C. for 16 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and water (200 m) was added. The aqueous phase was extracted with ethyl acetate (100 mL), and the combined organic phases were washed with water (2×100 mL) and dried (MgSO4). The organic phase was concentrated in vacuo to give 2.5 g of trans-4-[(4-hydroxycyclohexylamino)methyl]benzoic acid methyl ester.

Workup

  1. additionwas added
  2. extractionThe aqueous phase was extracted with ethyl acetate (100 mL)
  3. washthe combined organic phases were washed with water (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-1bdad0fb91ae45e68dd12d1b1093db07
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

Loading…