Ether hydrochloride → HCID 43149929, compound

HRID 2095407Notes

Reaction equation

HRID 2095407 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCOCC>CO>[CH:17]1([O:16][CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 59371572HCID 59371572, compound

Product 1

HCID 43149929HCID 43149929, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-[2-(cyclohexyloxy)ethyl]piperidine (182 mg, 0.59 mmol) in MeOH (2 mL) was added 2N anhydrous HCl/ether (0.75 mL, 1.5 mmol). The reaction mixture was stirred overnight. After evaporation, the residue was dissolved in deionized water. EtOAc was used to wash the aqueous layer before the pH was altered to approx. 9-10. The aqueous layer was extracted three times with CH2Cl2 and dried over Na2SO4. After evaporation, the product (38.0 mg, 30%) was obtained as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 3.46-3.29 (m, 2H), 3.16 (1, 2H), 3.02 (m, 2H), 2.56 (m, 2H), 2.17 (br, 1H), 1.88 (m, 2H), 1.71-1.64 (m, 4H), 1.52-1.42 (m, 4H), 1.25-1.22 (m, 3H), 1.99-1.13 (m, 2H), 1.11-1.08 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ 64.8, 46.3, 37.0, 33.2, 32.8, 32.0, 27.2, 25.4, 23.9.

Workup

  1. customAfter evaporation
  2. dissolutionthe residue was dissolved in deionized water
  3. washto wash the aqueous layer before the pH
  4. extractionThe aqueous layer was extracted three times with CH2Cl2
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation

Sources & evidence

ORD record
ord-2061f07d46174efc9235fa9c1eb1ee3e
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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