Water → HCID 20453410, compound

HRID 1462504Notes

Reaction equation

HRID 1462504 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C:7]([N:15]=[C:16]=O)([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)[CH2:6][CH2:5]2)[O:3]C1.O1CCCC1.O.[OH-].[Na+]>[H-].[Al+3].[Li+].[H-].[H-].[H-]>[CH3:16][NH:15][C:7]1([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962Water2×HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 12595566HCID 12595566, compound

Product 1

HCID 20453410HCID 20453410, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 21226445Aluminium lithium hydrideSolvent

Procedure

A solution of 2.21 g. (8.3 mmole) of 4-isocyanato-4-(2-thienyl)cyclohexanone ethylene ketal in 40 ml. tetrahydrofuran (THF) is added to a suspension of 0.32 g. (8.4 mmole) in lithium aluminum hydride (LAN) in 5 ml. THF. Following 4 hours' stirring under reflux the mixture is cooled in ice. There is then added in turn 0.32 ml. water, 0.32 ml. 15% NaOH and 0.96 ml. water. The inorganic gel is collected on a filter and the filtrate taken to dryness. A solution of the residue in a small amount of ether is treated with a just-sufficient amount of 3 N hydrogen chloride in ether. The precipitated salt is recrystallized from methylene chloride:ethyl acetate to afford 0.84 g. (35% yield) of 4-methylamino-4-(2-thienyl)cyclohexanone, ethylene ketal hydrochloride, m.p. 211°-214° C.

Workup

  1. temperatureunder reflux the mixture
  2. temperatureis cooled in ice
  3. additionThere is then added in turn 0.32 ml
  4. customThe inorganic gel is collected on
  5. filtrationa filter
  6. additionA solution of the residue in a small amount of ether is treated with a just-sufficient amount of 3 N hydrogen chloride in ether
  7. customThe precipitated salt is recrystallized from methylene chloride
  8. customethyl acetate to afford 0.84 g

Sources & evidence

ORD record
ord-51b902e6913a4c5497297bd8aec126bb
Source dataset
uspto-grants-1984_07
Patent number
US04460604

Reaction notes

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