Toluene → HCID 19370246, compound

HRID 129731Notes

Reaction equation

HRID 129731 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15]Cl)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C1(C)C=CC=CC=1>O>[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 4837PiperazineHCID 19370275HCID 19370275, compound

Product 1

HCID 19370246HCID 19370246, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.2 g (7 mmole) of 4-(diphenylmethylene)-1-(2-chloroethyl)piperidine [prepared as described in step (b) above], 4.8 g (55.7 mmole) of anhydrous piperazine and 60 ml of toluene was heated under reflux overnight. At the end of this time, water was added to the reaction mixture, the toluene layer was separated, and a 10% w/v aqueous solution of acetic acid was added to the toluene layer to extract the desired compound. The aqueous layer was separated and made alkaline by the addition of a 10% w/v aqueous solution of sodium hydroxide, after which it was extracted with diethyl ether. The diethyl ether was removed by distillation under reduced pressure, to obtain the title compound as crystals, melting at 73°-75° C., in a yield of 86%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customthe toluene layer was separated
  4. additiona 10% w/v aqueous solution of acetic acid was added to the toluene layer
  5. extractionto extract the desired compound
  6. customThe aqueous layer was separated
  7. additionby the addition of a 10% w/v aqueous solution of sodium hydroxide
  8. extractionafter which it was extracted with diethyl ether
  9. customThe diethyl ether was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-090ebeb1e7a542ab97ac6b0822f82c1f
Source dataset
uspto-grants-1995_11
Patent number
US05470851

Reaction notes

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