1-(1,4-Dioxaspiro[4.5]dec-7ylmethyl)-1,2,3,6-tetrahydro-4-phenylpyridine → 3-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]cyclohexanone

HRID 1034197Notes

Reaction equation

HRID 1034197 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][N:12]3[CH2:17][CH:16]=[C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:14][CH2:13]3)[CH2:6]2)[O:4]CC1>CC(C)=O.Cl>[C:18]1([C:15]2[CH2:16][CH2:17][N:12]([CH2:11][CH:7]3[CH2:8][CH2:9][CH2:10][C:5](=[O:4])[CH2:6]3)[CH2:13][CH:14]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 102450751-(1,4-Dioxaspiro[4.5]dec-7ylmethyl)-1,2,3,6-tetrahydro-4-phenylpyridine

Product 1

HCID 117778783-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]cyclohexanoneYield 88.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1-(1,4-dioxaspiro[4.5]dec-7ylmethyl)-1,2,3,6-tetrahydro-4-phenylpyridine (Step C) (90.4 g) in 500 mL of acetone and 500 mL of 10% aqueous hydrochloric acid solution is refluxed, under nitrogen, for 3 hours. The solvent is evaporated in vacuo and partitioned into ethyl acetate/dilute ammonium hydroxide solution. The organic extract is dried over magnesium sulfate and concentrated, leaving the title compound (68.9 g) as a light pink solid; mp 56°-59° C. Mass spectrum (MS) electron ionization (EI) 269 (m, 41%), 172 (100%).

Workup

  1. customThe solvent is evaporated in vacuo
  2. custompartitioned into ethyl acetate/dilute ammonium hydroxide solution
  3. extractionThe organic extract
  4. dry with materialis dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3a881b1b0e2b4f1fb2061b249708639b
Source dataset
uspto-grants-1994_05
Patent number
US05314896

Reaction notes

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