Potassium Carbonate → HCID 178514907, compound

HRID 1778671Notes

Reaction equation

HRID 1778671 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([CH2:12]Br)[CH:3]=1.Cl.[NH2:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:8])[N:15]([C@H:16]1[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18][CH2:17]1)[CH2:12]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoateHCID 178479278HCID 178479278, compound

Product 1

HCID 178514907HCID 178514907, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 4-bromo-2-(bromomethyl)benzoate (0.500 g, 1.62 mmol), trans-4-aminocyclohexanol hydrochloride (0.295 g, 1.95 mmol), and potassium carbonate (0.44 g, 3.2 mmol) in ethanol (5.0 mL) was stirred in a sealed vial at 50° C. for 4 h. After cooling, the mixture was diluted with ethyl acetate (10 mL), and was filtered. The filtrate was concentrated under reduced pressure. The residue was triturated with ethyl ether (3 mL). The precipitates were collected by filtration and washed with ethyl ether to afford the desired product. LCMS (M+H)+=309.9/312.0.

Workup

  1. temperatureAfter cooling
  2. filtrationwas filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was triturated with ethyl ether (3 mL)
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with ethyl ether

Sources & evidence

ORD record
ord-4e03f9cc3b6444dd9021597d034f9f5b
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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