HCID 12831592, compound → HCID 12831593, compound

HRID 1446814Notes

Reaction equation

HRID 1446814 reaction equation
[C:1]1([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2(O)[CH2:19][CH2:18][CH:17]([N:20]([CH3:22])[CH3:21])[CH2:16][CH2:15]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.Cl>[C:1]1([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[CH2:19][CH2:18][CH:17]([N:20]([CH3:21])[CH3:22])[CH2:16][CH:15]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 12831592HCID 12831592, compound

Product 1

HCID 12831593HCID 12831593, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 7.0 g of 1-[2-(phenylmethyl)phenyl]-4-dimethylaminocyclohexanol of Example 1 in 30 ml of acetic acid and 3 ml of hydrochloric acid (concentrated) is heated to reflux for 41/2 hours. After the contents are allowed to stand at 5° C. for 3 days, the solvent is evaporated off and the residue is dissolved in 50 ml of water. The solution is filtered and made alkaline with a slight excess of 50% aqueous NaOH. After cooling, the product is collected by suction filtration, and the filter cake is washed with water and dried in vacuo over P2O5 at 40° C. to yield 6.57 g (99.7% yield) of 1-[2-(phenylmethyl)phenyl]-4-dimethylaminocyclohex-1-ene m.p. 44°-45° C.

Workup

  1. temperatureto reflux for 41/2 hours
  2. customthe solvent is evaporated off
  3. dissolutionthe residue is dissolved in 50 ml of water
  4. filtrationThe solution is filtered
  5. temperatureAfter cooling
  6. filtrationthe product is collected by suction filtration
  7. washthe filter cake is washed with water
  8. dry with materialdried in vacuo over P2O5 at 40° C.

Sources & evidence

ORD record
ord-cb4c78a1f2974d1392e56973293e87a1
Source dataset
uspto-grants-1982_02
Patent number
US04313959

Reaction notes

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