Diethyl Ether → HCID 21519682, compound

HRID 1283301Notes

Reaction equation

HRID 1283301 reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]1=2.C(OCC)C.[CH3:20][N:21]1[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[CH2:22]1>CCCCCC>[CH3:20][N:21]1[CH2:26][CH2:25][CH2:24][C:23]([C:10]2[S:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]=2)([OH:27])[CH2:22]1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 7221Benzo(B)ThiopheneHCID 796563-Piperidinone, 1-methyl-HCID 178418339Butyllithium

Product 1

HCID 21519682HCID 21519682, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

26.5 ml of a 2N solution of n-butyllithium in hexane is added dropwise within 30 minutes to a solution of 7.0 g of benzo[b]thiophene in 50 ml of abs. diethyl ether at a reaction temperature of 5° to 10°. The solution is then stirred for a further 1 hour at 0°. There is then added dropwise, in the course of 30 minutes, a solution of 5.9 g of 1-methyl-3-piperidone in 50 ml of abs. diethyl ether, with the reaction temperature being maintained at 0° by external cooling. The reaction solution is stirred for a further 15 hours at room temperature, and is then poured, with stirring, onto 100 g of ice; the aqueous phase is separated, and extracted 3 times with 100 ml of ethyl acetate each time. The combined organic extracts are dried with sodium sulphate, filtered under suction and concentrated by evaporation. The residue is dissolved in 250 ml of 2N hydrochloric acid, and the acid solution is washed with diethyl ether. The aqueous solution is subsequently brought to a pH-value of 12 by the addition of 10 sodium hydroxide solution, and extracted with 500 ml of chloroform. The chloroform solution is dried with sodium sulphate, filtered with suction and concentrated by evaporation to obtain crude 1-methyl-3-(benzo[b]thien-2-yl)-3-piperidinol; the oxalate thereof is prepared, for example, from 1.8 g of free base in ethyl actate and 0.7 g of oxalic acid in 10 ml of ethyl acetate, and it melts at 165°-168° after recrystallisation from ethyl acetate.

Workup

  1. customat a reaction temperature of 5° to 10°
  2. additionThere is then added dropwise, in the course of 30 minutes
  3. stirringThe reaction solution is stirred for a further 15 hours at room temperature
  4. additionis then poured
  5. customthe aqueous phase is separated
  6. extractionextracted 3 times with 100 ml of ethyl acetate each time
  7. dry with materialThe combined organic extracts are dried with sodium sulphate
  8. filtrationfiltered under suction
  9. concentrationconcentrated by evaporation
  10. dissolutionThe residue is dissolved in 250 ml of 2N hydrochloric acid
  11. washthe acid solution is washed with diethyl ether
  12. additionThe aqueous solution is subsequently brought to a pH-value of 12 by the addition of 10 sodium hydroxide solution
  13. extractionextracted with 500 ml of chloroform
  14. dry with materialThe chloroform solution is dried with sodium sulphate
  15. filtrationfiltered with suction
  16. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5f6b7c60c7814f8abcf291de882b31be
Source dataset
uspto-grants-1976_08
Patent number
US03974280

Reaction notes

Loading…