Methanol → HCID 53758168, compound

HRID 1973253Notes

Reaction equation

HRID 1973253 reaction equation
[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]2[CH2:13][CH2:12][NH:11][C:10]([CH3:25])([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[CH2:34]1[O:36][CH2:35]1>C1C=CC=CC=1>[C:26]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:34][CH2:35][OH:36])[C:10]([CH3:25])([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)[CH2:9]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6354Ethylene OxideHCID 21428563HCID 21428563, compound

Product 1

HCID 53758168HCID 53758168, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

50 g of 1-diphenylmethyl-3-methyl-3-(3,4-dimethoxybenzyl)-piperazine (cf. Example 2) are dissolved in 200 ml of benzene and 400 ml of methanol and heated for 48 hours in a pressure vessel at 60° C. with addition of 22 g of ethylene oxide. Subsequently, the solution is evaporated to dryness. The residue is dissolved in 500 ml of diethylether, combined with 60 ml of 2N HCl, and vigorously stirred. The organic phase is separated and washed halide-free with water. The aqueous acid extract is alkalized with ammonium hydroxide solution and extracted with diethyl ether. The extract is dried, filtered, and the solvent is removed by distillation. 54 g (98 percent of theory) of 1-diphenylmethyl-3-methyl-3-(3,4-dimethoxybenzyl)-4-hydroxyethylpiperazine are obtained as a colorless resin.

Workup

  1. customSubsequently, the solution is evaporated to dryness
  2. dissolutionThe residue is dissolved in 500 ml of diethylether
  3. customThe organic phase is separated
  4. washwashed halide-free with water
  5. extractionThe aqueous acid extract
  6. extractionextracted with diethyl ether
  7. customThe extract is dried
  8. filtrationfiltered
  9. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-c758af0b7ec8441f9eb55b9b9c7e9390
Source dataset
uspto-grants-1976_12
Patent number
US03996360

Reaction notes

Loading…