Hydrochloric Acid → HCID 24897936, compound

HRID 12933Notes

Reaction equation

HRID 12933 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].Cl.[CH2:14](Cl)[CH3:15].[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+].Cl>CO.CCOCC>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:21][CH2:22][N:17]2[CH2:15][CH2:14][CH2:20][CH2:19][CH2:18]2)=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 21333162HCID 21333162, compoundHCID 226340454-But-2-ynyloxy-phenol

Product 1

HCID 24897936HCID 24897936, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of the product from step 1 (200 mg, 1.23 mmol) in MeOH (10 mL) was added piperidine ethyl chloride hydrochloride (227 mg, 1.23 mmol), and K2CO3 (679 mg, 4.92 mmol), and the resulting mixture was refluxed for 10 h. Solvent was removed in vacuo and the crude product was dissolved in EtOAc and partitioned with water. Organic layer was separated and dried over anhydroua Na2SO4. Solvent was removed in vacuo to obtain a thick oil, which was added 2M HCl in ether. Solvent was decanted and the solid was triturated with ether to obtain the title product (100 mg, 30%); MS m/z 274.4 (M+H) 99%: 1H NMR (DMSO-d6, 400 MHz) δ 1.39 (1H, m), 1.67-1.82 (8H, m), 2.97 (2H, m), 3.41-3.50 (1H, m), 3.75 (1H, br m), 4.31 (2H, d, J=5.2 Hz), 4.67 (2H, s).

Workup

  1. temperaturethe resulting mixture was refluxed for 10 h
  2. customSolvent was removed in vacuo
  3. dissolutionthe crude product was dissolved in EtOAc
  4. custompartitioned with water
  5. customOrganic layer was separated
  6. dry with materialdried over anhydroua Na2SO4
  7. customSolvent was removed in vacuo
  8. customto obtain a thick oil, which
  9. customSolvent was decanted
  10. customthe solid was triturated with ether

Sources & evidence

ORD record
ord-9e4f6b917c0841efba7ace796dc89aef
Source dataset
uspto-grants-2010_06
Patent number
US07728032B2

Reaction notes

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