2-Methylbenzenesulfonic acid → HCID 54517547, compound

HRID 2286496Notes

Reaction equation

HRID 2286496 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][C:8](=O)[CH2:9]3)=[CH:4][C:3]=2[O:2]1.[N:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][C:8]([N:24]4[CH2:25][CH2:26][N:21]([C:16]5[N:15]=[CH:20][CH:19]=[CH:18][N:17]=5)[CH2:22][CH2:23]4)=[CH:9]3)=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 887471-(2-Pyrimidinyl)piperazineHCID 12843073HCID 12843073, compound

Product 1

HCID 54517547HCID 54517547, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.8 g of 6,7-methylenedioxy-2-tetralone and 3.3 g of 1-(2-pyrimidinyl) piperazine in 100 ml of anhydrous toluene was boiled for 30 minutes in the presence of 100 mg of p.toluenesulphonic acid, in a Dean and Stark apparatus. When the theoretical quantity of water was collected, the solution was cooled and washed with twice 20 ml of water. The solution was then decanted off, and the solvent was evaporated under reduced pressure. The residue was taken up with petroleum ether, and there were obtained 6.4 g of 1-(6,7-methylenedioxy-3,4-dihydro-2-naphthyl)-4-(2-pyrimidinyl) piperazine, beige crystals melting at 155°-160° C.

Workup

  1. customWhen the theoretical quantity of water was collected
  2. temperaturethe solution was cooled
  3. washwashed with twice 20 ml of water
  4. customThe solution was then decanted off
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ee0b79756eda4237a40b2e14c87a4d53
Source dataset
uspto-grants-1981_05
Patent number
US04267178

Reaction notes

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