Tetrahydrofuran → HCID 178511499, compound

HRID 1657566Notes

Reaction equation

HRID 1657566 reaction equation
C(O)(=O)C.[C:5]1([CH:11]2[CH2:16][CH2:15][C:14](=[N:17]O)[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O1CCCC1>C(O)(C)(C)C>[C:5]1([C@H:11]2[CH2:12][CH2:13][C@H:14]([NH2:17])[CH2:15][CH2:16]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 86733518HCID 86733518, compound

Product 1

HCID 178511499HCID 178511499, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Into a solution of 8.58 g. of 4-phenylcyclohexanone oxime acetate (prepared in Example 79) in 90 ml. of tetrahydrofuran and 27 ml. of t-butanol, 350 ml. of ammonia is distilled from over sodium. To this there is added 1.9 g. of lithium in three portions at a rate that the blue color just persists. When the final blue color fades, 10 g. of solid ammonium chloride is added and the solvent is then evaporated with a stream of nitrogen. The residue is dissolved in ether and aqueous N-sodium hydroxide solution. The organic layer is separated, washed with water and brine and then taken to dryness to give a residue of trans 4-phenylcyclohexylamine. The residue is dissolved in a small amount of ether and treated with an excess of 4.9N hydrogen chloride in ether. The precipitate that forms is collected on a filter to yield 7.9 g. of trans 4-phenylcyclohexylamine hydrochloride. A sample of identical material previously prepared melts above 300° C.

Workup

  1. distillationof ammonia is distilled from over sodium
  2. additionTo this there is added 1.9 g
  3. additionof solid ammonium chloride is added
  4. customthe solvent is then evaporated with a stream of nitrogen
  5. dissolutionThe residue is dissolved in ether
  6. customThe organic layer is separated
  7. washwashed with water and brine

Sources & evidence

ORD record
ord-a4311261a8604f4bb730bf56f12ccb29
Source dataset
uspto-grants-1976_06
Patent number
US03960961

Reaction notes

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