Hydrochloric Acid → HCID 68146490, compound

HRID 1730168Notes

Reaction equation

HRID 1730168 reaction equation
[CH3:1][C:2]1([CH3:19])[C@@H:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[CH2:5][C@@H:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:3]1.S(=O)(=O)(O)O.[OH-].[Na+].N1CCCC1.[ClH:32].[N+:33]([O-])([OH:35])=[O:34]>CCOCC.C(O)C>[ClH:32].[ClH:32].[CH3:1][C:2]1([CH3:19])[C@@H:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[CH2:5][C@@H:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:33]([O-:35])=[O:34])[CH:14]=2)[NH:3]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 12621383HCID 12621383, compound

Product 1

HCID 68146490HCID 68146490, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

20 G. of 4-(cis-2,2-dimethyl-5-phenyl-3-pyrrolidinyl)-pyridine (racemate) are dissolved under cool temperatures (5°-10° C.) in concentrated nitric acid and 50 ml. of cool concentrated sulfuric acid are slowly added. Thereafter, the reaction mixture is stirred for about 1 hour at 10°-15° C. and then poured on ice. The pH of the reaction mixture is then adjusted to pH 8-9 with 3N sodium hydroxide, also in the cold, and exhaustively extracted with methylenechloride. The combined extracts are dried over sodium sulfate and evaporated in a water pump vacuum to dryness. The product thereby obtained is a mixture of pyrrolidine with para and meta nitrophenyl substituents. The mixture is dissolved in 400 ml. warm ethanol. After the addition of 25 ml. concentrated hydrochloric acid and some ether, a mixture of dihydrochlorides (m-nitrophenyl and p-nitrophenyl, 8 to 2) is obtained. Fractional crystallization from ethanol yields 4-[cis-2,2-dimethyl-5-(m-nitrophenyl)-3-pyrrolidinyl]-pyridine dihydrochloride (racemate) with a melting point of 229°-232° C. (decomp.).

Workup

  1. additionare slowly added
  2. additionpoured on ice
  3. extractionalso in the cold, and exhaustively extracted with methylenechloride
  4. dry with materialThe combined extracts are dried over sodium sulfate
  5. customevaporated in a water pump vacuum to dryness
  6. customThe product thereby obtained
  7. dissolutionThe mixture is dissolved in 400 ml
  8. additionAfter the addition of 25 ml
  9. customis obtained
  10. customFractional crystallization from ethanol

Sources & evidence

ORD record
ord-41c1d75c9c5644f1844b6352ee5b116a
Source dataset
uspto-grants-1976_11
Patent number
US03991197

Reaction notes

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