Sodium Chloride → 8-Pyrrolidinyl-5,6,7,8-tetrahydroquinoline

HRID 1194697Notes

Reaction equation

HRID 1194697 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH:7]1[C:16]2[N:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:10][CH2:9][CH2:8]1.[Cl-].[Na+]>O>[N:1]1([CH:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:10][CH2:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 31268PyrrolidineHCID 137121808-Chloro-5,6,7,8-tetrahydroquinoline

Product 1

HCID 139833798-Pyrrolidinyl-5,6,7,8-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Over a period of 7 minutes with stirring and while allowing it to heat up, 50 ml of pyrrolidine were added to a solution of 20 g of 8-chloro-5,6,7,8-tetrahydroquinoline in 50 ml of water. The temperature reached 57° C. at the end of the introduction and stirring was continued for 1 hour at this temperature. The temperature was then allowed to return to 20° C. and the reaction medium was saturated with sodium chloride and then was extracted with ether. The combined organic phases were dried and the solvents were eliminated under reduced pressure to obtain 20.22 g of 8-pyrrolidinyl-5,6,7,8-tetrahydroquinoline in the form of an oil.

Workup

  1. temperatureto heat up
  2. customreached 57° C. at the end of the introduction
  3. stirringstirring
  4. waitwas continued for 1 hour at this temperature
  5. customto return to 20° C.
  6. extractionwas extracted with ether
  7. customThe combined organic phases were dried

Sources & evidence

ORD record
ord-bdc91502ed664d07af8ab81ac6217dff
Source dataset
uspto-grants-1989_03
Patent number
US04816465

Reaction notes

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