Hydrochloric Acid → HCID 21994217, compound

HRID 725914Notes

Reaction equation

HRID 725914 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.COC1C=CC=CC=1C([N:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:25][CH2:24]1)C#N.Cl.C[CH2:37][O:38][CH2:39][CH3:40]>O1CCCC1.O>[CH3:37][O:38][C:39]1[CH:40]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:30][CH2:29][NH:26][N:23]1[CH2:24][CH2:25][N:26]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:27][CH2:28]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 15288971HCID 15288971, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21994217HCID 21994217, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

2.3 g (60 mmol) of Lithium aluminium hydride are suspended in 100 ml of ether under a nitrogen atmosphere and cooled to about -10° C. 1.6 ml (30 mmol) of conc. sulphuric acid are carefully added dropwise thereto, with further cooling, and the resulting mixture is stirred for 1.5 hours at about -5° C. Then a solution of 9.2 g (30 mmol) of (2-methoxyphenyl)-(4-phenylpiperazine-1-yl)-acetonitrile in 50 ml of tetrahydrofuran is slowly added dropwise. The mixture is allowed to come up to ambient temperature and is then refluxed for about 10 minutes. It is then allowed to cool and stirred overnight at ambient temperature. A mixture of 8 ml of tetrahydrofuran and 8 ml of water is then added, initially very carefully, to the grey suspension, whilst cooling with ice, and then 165 ml of 2N hydrochloric acid are added. The reaction mixture is then washed twice with 70 ml of ether and the ethereal phases are discarded. 18.2 g of Seignette salt and 45 ml of conc. sodium hydroxide solution are then added. The mixture is extracted four times with 70 ml of ether, the combined organic phases are dried over sodium sulfate and the solvent is eliminated in vacuo. 8.6 g of 2-(2-methoxyphenyl)-(4-phenylpiperazine-1-yl)-ethylamine are obtained (92% yield) as a yellowish oil. There is no additional purification before the further reactions.

Workup

  1. customto come up to ambient temperature
  2. temperatureis then refluxed for about 10 minutes
  3. temperatureto cool
  4. stirringstirred overnight at ambient temperature
  5. additionis then added
  6. temperatureinitially very carefully, to the grey suspension, whilst cooling with ice
  7. washThe reaction mixture is then washed twice with 70 ml of ether
  8. addition18.2 g of Seignette salt and 45 ml of conc. sodium hydroxide solution are then added
  9. extractionThe mixture is extracted four times with 70 ml of ether
  10. dry with materialthe combined organic phases are dried over sodium sulfate

Sources & evidence

ORD record
ord-c8efbe310990406880a0b3d0e4b3da4a
Source dataset
uspto-grants-1998_01
Patent number
US05708006

Reaction notes

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