Benzaldehyde → HCID 10378303, compound

HRID 1195717Notes

Reaction equation

HRID 1195717 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:5]2=[N:6][CH:7]=1.C([Li])CCC.[CH:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>O1CCCC1.CCCCCC.C(OCC)C>[CH3:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:5]2=[N:6][C:7]=1[CH:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:25]

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 150070406,7,8,9-Tetrahydro-3-methyl-5H-cyclohepta[b]pyridineHCID 178418339Butyllithium

Product 1

HCID 10378303HCID 10378303, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Conditions

Temperature
0 °C

Procedure

6,7,8,9-Tetrahydro-3-methyl-5H-cyclohepta[b]pyridine (4.42 g, 0.025 m) in tetrahydrofuran (50 ml) was cooled to -40° C. under nitrogen and treated with n-butyl lithium in n-hexane (1.57 molar soln, 16 ml) and allowed to warm to 0° C. The solution was cooled to -70° C. and treated with a solution of benzaldehyde (4 ml) in tetrahydrofuran (10 ml) and allowed to warm to room temperature, then water and diethyl ether were added. The organic phase was separated and extracted with 2N hydrochloric acid. The acid phase was made basic with solid sodium carbonate and then extracted with chloroform. The combined chloroform extract was washed with water, dried (MgSO4) and evaporated under reduced pressure to give a gum. This was dissolved in n-hexane and the crystallised material collected by filtration. This was purified by chromatography on silica using diisopropyl ether:chloroform (9:1 by volume) as eluent. The isolated solid was triturated in diisopropyl ether give 1-(6,7,8,9-tetrahydro-3-methyl-5H-cyclohepta[b]pyrid-2-yl)-1-phenylmethanol (1.1 g) m.p. 130°-2° C.

Workup

  1. temperatureThe solution was cooled to -70° C.
  2. temperatureto warm to room temperature
  3. customThe organic phase was separated
  4. extractionextracted with 2N hydrochloric acid
  5. extractionextracted with chloroform
  6. extractionThe combined chloroform extract
  7. washwas washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated under reduced pressure
  10. customto give a gum
  11. filtrationthe crystallised material collected by filtration
  12. customThis was purified by chromatography on silica
  13. customThe isolated solid was triturated in diisopropyl ether

Sources & evidence

ORD record
ord-dbfef4e8700c47279d975b5de069deaa
Source dataset
uspto-grants-1992_05
Patent number
US05112832

Reaction notes

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