Ammonia → HCID 3044138, compound

HRID 2419009Notes

Reaction equation

HRID 2419009 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14](O)[CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.N>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 20316756HCID 20316756, compound

Product 1

HCID 3044138HCID 3044138, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

81 g of the compound produced in step (b) were dissolved in 500 ml of toluene and, to the solution so produced, was added a solution of 76 g of p-toluenesulphonic acid in the minimum quantity of water. The mixture was heated under reflux for about 20 hours, continuously removing the water formed. At the end of this time, the solution was cooled and poured into 2 liters of water, to which ammonia was added until the solution became alkaline. The organic phase was then separated, washed with water and dried with sodium sulphate. 66 g (yield 86%) of 3-chloro-4-cyclohexyl-1-(3-diethylamino-propen-1-yl)-benzene (hereinafter referred to as compound 933 CB) were obtained in the form of a light brown oil. This was dissolved in ether and reacted with a sufficient quantity of hydrochloric acid dissolved in the same solvent to produce 67 g of the hydrochloride having a melting point of 161° C.

Workup

  1. customso produced
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for about 20 hours
  4. customcontinuously removing the water
  5. customformed
  6. temperatureAt the end of this time, the solution was cooled
  7. additionwas added until the solution
  8. customThe organic phase was then separated
  9. washwashed with water
  10. dry with materialdried with sodium sulphate

Sources & evidence

ORD record
ord-88d82667ea87424e91990b31e853998c
Source dataset
uspto-grants-1978_08
Patent number
US04104383

Reaction notes

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