Ethanol → HCID 12805919, compound

HRID 904064Notes

Reaction equation

HRID 904064 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:13]([CH3:15])([CH3:14])[N+:12]([O-])=[C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10]2)=[CH:5][CH:4]=1.C(O)C>[Zn].C(O)=O>[CH3:1][N:2]([CH3:23])[C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:10][C@H:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:12][C:13]2([CH3:14])[CH3:15])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 23333472HCID 23333472, compound

Product 1

HCID 12805919HCID 12805919, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Procedure

47 G. of 4-(p-dimethylaminophenyl)-5,5-dimethyl-2-phenyl-1-pyrroline 1-oxide are dissolved in a mixture of 400 ml. of ethanol and 400 ml. of formic acid and treated portionwise while stirring with 80 g. of zinc powder. The temperature is held at 43° C. during this addition. Subsequently, the mixture is stirred for a further 2 hours, the zinc sludge is then filtered off and the filtrate evaporated under reduced pressure. The residue is taken up in water, neutralized with 3-N sodium hydroxide and extracted with ether. The ether phase is then dried over sodium sulfate and evaporated under reduced pressure. The residue is chromatographed on silica gel, elution being carried out first with pure benzene and then with benzene/acetone mixtures with increasing acetone content (up to 50% acetone). There is thus obtained trans-3-(p-dimethylaminophenyl)-2,2-dimethyl-5-phenyl-pyrrolidine which melts at 108°-109° C. after crystallization from n-hexane.

Workup

  1. additionThe temperature is held at 43° C. during this addition
  2. stirringSubsequently, the mixture is stirred for a further 2 hours
  3. filtrationthe zinc sludge is then filtered off
  4. customthe filtrate evaporated under reduced pressure
  5. extractionextracted with ether
  6. dry with materialThe ether phase is then dried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue is chromatographed on silica gel, elution
  9. customafter crystallization from n-hexane

Sources & evidence

ORD record
ord-6ce1a233a56a4b54b67b20be0d13407f
Source dataset
uspto-grants-1980_10
Patent number
US04230623

Reaction notes

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