Ethyl Acetate → HCID 178420355, compound

HRID 1403124Notes

Reaction equation

HRID 1403124 reaction equation
[CH2:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:24][CH2:25][CH2:26][O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1.[OH-].[K+].C(OCC)(=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C(C)=CC=CC=1.O>[CH2:16]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][CH2:24][CH2:25][CH2:26][O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH2:11][CH2:10]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 178521611HCID 178521611, compound

Product 1

HCID 178420355HCID 178420355, compoundYield 58.7%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

trans-4-(Dibenzylamino)cyclohexanol (200 mg), 2-(3-bromopropoxy)tetrahydro-2H-pyran (604 mg), powder potassium hydroxide (179 mg), and tetrabutylammonium bromide (44 mg) were suspended in xylene (2 mL), followed by stirring at room temperature for 2 hours. To the reaction mixture were added ethyl acetate and water, and the organic layer was extracted and washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by amino silica gel column chromatography (hexane:ethyl acetate=100:0-80:20) to obtain trans-N,N-dibenzyl-4-[3-(tetrahydro-2H-pyran-2-yloxy)propoxy]cyclohexanamine (174 mg).

Workup

  1. extractionthe organic layer was extracted
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by amino silica gel column chromatography (hexane:ethyl acetate=100:0-80:20)

Sources & evidence

ORD record
ord-cd776acbb74148959030a293a27b182c
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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