Hydrochloric Acid → HCID 54574559, compound

HRID 2286497Notes

Reaction equation

HRID 2286497 reaction equation
Cl.[CH2:2]1[O:14][C:13]2[CH:12]=[C:11]3[C:6]([CH2:7][CH2:8][C:9]([N:15]4[CH2:20][CH2:19][N:18]([C:21]5[N:26]=[CH:25][CH:24]=[CH:23][N:22]=5)[CH2:17][CH2:16]4)=[CH:10]3)=[CH:5][C:4]=2[O:3]1>O1CCCC1>[CH2:2]1[O:14][C:13]2[CH:12]=[C:11]3[C:6]([CH2:7][CH2:8][CH:9]([N:15]4[CH2:20][CH2:19][N:18]([C:21]5[N:22]=[CH:23][CH:24]=[CH:25][N:26]=5)[CH2:17][CH2:16]4)[CH2:10]3)=[CH:5][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54517547HCID 54517547, compound

Product 1

HCID 54574559HCID 54574559, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

There were added 2 ml of a solution 5 N of HCl in tetrahydrofuran to a solution of 3.35 g of 1-(6,7-methylenedioxy-3,4-dihydro-2-naphthyl)-4-(2-pyrimidinyl) piperazine previously obtained, in 100 ml of anhydrous tetrahydrofuran. The hydrochloride of the enamine precipitated, and there were added, to the so-obtained suspension, 10 ml of a normal solution of sodium cyanoborohydride in tetrahydrofuran. The precipitate was then immediately dissolved and the solution was decolourised. 30 minutes later, the solvent was evaporated off and the residue was taken up with a normal sodium hydroxide solution, then extracted with chloroform. The chloroformic solution was then evaporated under reduced pressure and the viscous residue was taken up with 30 ml of anhydrous ethanol. The product crystallized and there were obtained 2.1 g of 1-(6,7-methylenedioxy-1,2,3,4-tetrahydro-2-naphthyl)-4-(2-pyrimidinyl) piperazine, beige crystals melting at 134°-135° C. The corresponding monomethanesulfonate melts at 218°-225° C.

Workup

  1. customThe hydrochloride of the enamine precipitated
  2. additionthere were added, to the so-obtained suspension, 10 ml of a normal solution of sodium cyanoborohydride in tetrahydrofuran
  3. dissolutionThe precipitate was then immediately dissolved
  4. custom30 minutes later, the solvent was evaporated off
  5. extractionextracted with chloroform
  6. customThe chloroformic solution was then evaporated under reduced pressure
  7. customThe product crystallized

Sources & evidence

ORD record
ord-7cbb78c37ece4f1382a7e1cb1c893caf
Source dataset
uspto-grants-1981_05
Patent number
US04267178

Reaction notes

Loading…