Methane → 3-[(2-Phenylamino-1-pyrrolidinyl)methyl]indole

HRID 128251Notes

Reaction equation

HRID 128251 reaction equation
P(Cl)(Cl)(Cl)=O.N(CC1C2C(=CC=CC=2)NC=1)C1C=CC=CC=1.N1CCCC1=O.C(N(CC)CC)C.N1CCCC=1N(CC1C2C(=CC=CC=2)NC=1)C1C=CC=CC=1.C.[C:59]1([N:65]=[C:66]2[CH2:70][CH2:69][CH2:68][N:67]2[CH2:71][C:72]2[C:80]3[C:75](=[CH:76][CH:77]=[CH:78][CH:79]=3)[NH:74][CH:73]=2)[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1>C(O)C.ClCCCl>[C:59]1([NH:65][CH:66]2[CH2:70][CH2:69][CH2:68][N:67]2[CH2:71][C:72]2[C:80]3[C:75](=[CH:76][CH:77]=[CH:78][CH:79]=3)[NH:74][CH:73]=2)[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=1

Participants

10

Reactant 7

HCID 297MethaneHCID 8471TriethylamineHCID 120252-PyrrolidoneHCID 24813Phosphorus oxychlorideHCID 107042713-(Anilinomethyl)indoleHCID 205097203-[[N-(1-pyrrolin-2-yl)anilino]methyl]indoleHCID 205097693-[(2-Phenylimino-1-pyrrolidinyl)methyl]indole

Product 1

HCID 205097893-[(2-Phenylamino-1-pyrrolidinyl)methyl]indole

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 702EthanolSolvent

Procedure

Phosphorus oxychloride (7.67 g., 0.05 mole), 3-(anilinomethyl)indole (11.1 g., 0.05 mole), 2-pyrrolidinone (4.26 g., 0.05 mole) and triethylamine (5.06 g., 0.05 mole) in 100 ml. of 1,2-dichloroethane reacted according to the procedure of Example 35 provide a total of 6.4 g. of crude 3-[[N-(1-pyrrolin-2-yl)anilino]methyl]indole as the free base. The crude free base is taken up in ethanol and refluxed for 6 hr., treated with decolorizing charcoal and filtered. Concentration of the ethanol filtrate to about 20 ml. provides on standing a solid which crystallized from ethanol affords 2.75 g. of analytically pure 3-[(2-phenylimino-1-pyrrolidinyl)methyl]indole m.p. 150°-151° C. (corr.), characterized by the formula: ##STR31##

Workup

  1. customprovide a total of 6.4 g
  2. temperaturerefluxed for 6 hr
  3. filtrationfiltered
  4. customprovides
  5. customcrystallized from ethanol
  6. customaffords 2.75 g

Sources & evidence

ORD record
ord-3dec30e25a60405895395a84128b0077
Source dataset
uspto-grants-1981_03
Patent number
US04259238

Reaction notes

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