Sodium borohydride → Benzenamine, 4-(5,5-dimethyl-4-(4-pyridinyl)-2-pyrrolidinyl)-, cis-(+-)-

HRID 1730165Notes

Reaction equation

HRID 1730165 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[C:12]([CH3:22])([CH3:21])[N:11]=2)=[CH:6][CH:5]=1>CO>[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[NH:11][C:12]([CH3:22])([CH3:21])[C@@H:13]([C:15]3[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=3)[CH2:14]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 12621377HCID 12621377, compound

Product 1

HCID 3045823Benzenamine, 4-(5,5-dimethyl-4-(4-pyridinyl)-2-pyrrolidinyl)-, cis-(+-)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.55 G. of sodium borohydride are added to a solution of 1.85 g. of 4-[2-(p-aminophenyl)-5,5-dimethyl-1-pyrrolin-4-yl]-pyridine in 18.5 ml. of methanol and the mixture is stirred at room temperature for 2 hours. Then, an additional 0.55 g. of sodium borohydride are added and the reaction mixture is left to stand at room temperature overnight. The reaction mixture is then evaporated under reduced pressure and the resulting residue taken up in water and extracted three times with methylene chloride. The organic phase is dried over sodium sulfate and evaporated under reduced pressure. The resulting crude product is chromatographed on silica gel with chloroform/methanol/ethyl acetate/ammonia (60:10:2:1). The material obtained, after crystallization with ether, yields 4-[cis-5-(p-aminophenyl)-2,2-dimethyl-3-pyrrolidinyl]-pyridine of melting point 119°-120° C. The trihydrochloride, recrystallized from methanol/ether, has a melting point of 223°-226° C.

Workup

  1. waitthe reaction mixture is left
  2. customThe reaction mixture is then evaporated under reduced pressure
  3. extractionextracted three times with methylene chloride
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting crude product is chromatographed on silica gel with chloroform/methanol/ethyl acetate/ammonia (60:10:2:1)
  7. customThe material obtained
  8. customafter crystallization with ether

Sources & evidence

ORD record
ord-74d1c5f68f374f84a7eb08f9cf5a7c0e
Source dataset
uspto-grants-1976_11
Patent number
US03991197

Reaction notes

Loading…