Water → HCID 22678438, compound

HRID 1837717Notes

Reaction equation

HRID 1837717 reaction equation
C([Li])CCC.[CH2:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1Br.[CH2:21]([N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][CH:35]=[O:36])[CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>O1CCCC1>[CH2:21]([N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][CH:35]([OH:36])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][CH2:12][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:6]2)[CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 100136024-Piperidineacetaldehyde, 1-(phenylmethyl)-HCID 22678555HCID 22678555, compoundHCID 178418339Butyllithium

Product 1

HCID 22678438HCID 22678438, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

10 ml of tetrahydrofuran was cooled to −78° C., 5.11 ml of n-butyllithium (1.6 M, hexane solution) was added thereto, and the mixture was stirred. A solution of 2.000 g of (2-cyclohexylmethyloxy)bromobenzene dissolved in 5 ml of tetrahydrofuran was added dropwise thereinto. After one hour, a solution of 1.93 g of 1-benzyl-4-piperidineacetaldehyde dissolved in 5 ml of tetrahydrofuran was added dropwise thereinto, and the mixture was further stirred for one hour. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by NH form silica gel column chromatography (n-hexane:ethyl acetate=4:1), to give 2.986 g of the title compound as a colorless oil.

Workup

  1. additionwas added dropwise
  2. additionwas added dropwise
  3. stirringthe mixture was further stirred for one hour
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe crude product was purified by NH
  9. customform silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-556d149862154905a93d913b3cf36aaf
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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