Water → HCID 10039384, compound

HRID 1110350Notes

Reaction equation

HRID 1110350 reaction equation
C([Li])CCC.[CH3:6][C:7]1[N:12]=[C:11]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:10]2=[CH:9][CH:8]=1.[CH3:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1.O>CCCCCC.C1(C)C=CC=CC=1>[N:12]1[C:7]([CH2:6][CH:23]([C:22]2[CH:25]=[CH:26][C:19]([CH3:18])=[CH:20][CH:21]=2)[OH:24])=[CH:8][CH:9]=[C:10]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:11]=12

Participants

7

Reactant 4

HCID 962WaterHCID 77254-MethylbenzaldehydeHCID 12259432HCID 12259432, compoundHCID 178418339Butyllithium

Product 1

HCID 10039384HCID 10039384, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 1.6M n-butyl lithium in n-hexane (7.2 ml) in toluene (25 ml), at -20° C. under nitrogen, was added a solution of 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine (1.7 g 0.01 m) in toluene (5 ml). The solution was left to stir at -20° C. for 0.75 hours, then blown over into a solution of 4-methylbenzaldehyde (1.5 g). The solution was allowed to warm to room temperature and water added. The toluene phase was extracted with 2N hydrochloric acid and this was basified with solid potassium carbonate and then extracted with dichloromethane. The combined dichloromethane extracts were washed with water dried (MgSO4) and evaporated to give an oil. This was purified by chromatography on basic alumina using diisopropyl ether as eluent to give the title compound as an oil. This was dissolved in ether and treated with ethereal HCl to give a crystalline hydrochloride salt (1.2 g) m.p. 184°-6° C.

Workup

  1. waitThe solution was left
  2. temperatureto warm to room temperature
  3. extractionThe toluene phase was extracted with 2N hydrochloric acid
  4. extractionextracted with dichloromethane
  5. washThe combined dichloromethane extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give an oil
  9. customThis was purified by chromatography on basic alumina

Sources & evidence

ORD record
ord-d338751c3f4c48598d7a33946c5d412c
Source dataset
uspto-grants-1990_12
Patent number
US04975431

Reaction notes

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