Pyridine → HCID 20244935, compound

HRID 482686Notes

Reaction equation

HRID 482686 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][CH:6]1[C:18]2[NH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH2:9][CH2:8][NH:7]1.[C:19](Cl)(=[O:21])[CH3:20].N1C=CC=CC=1>CN(C)C=O>[Cl:2][CH2:3][CH2:4][CH2:5][CH:6]1[C:18]2[NH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH2:9][CH2:8][N:7]1[C:19](=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 202449631-(3'-Chloropropyl)-1,2,3,4-tetrahydro-beta-carboline hydrochloride

Product 1

HCID 20244935HCID 20244935, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

17.1 g (60 millimoles) of 1-(3'-chloropropyl)-1,2,3,4-tetrahydro-β-carboline hydrochloride were dissolved in 240 ml of dimethylformamide while heating, and the solution was then cooled to 5° C. in an ice bath. 11.5 g (150 millimoles) of acetyl chloride and immediately thereafter 23.7 g (300 millimoles) of pyridine were added dropwise to the thoroughly stirred solution, the temperature not rising above 5° C. during this operation. Thereafter, stirring was continued for a further 2 hours at this temperature, after which the reaction mixture was poured onto ice water. The precipitate was filtered off under suction and washed thoroughly with water. 16.9 g (97%) of crystals of melting point 166°-168° C. (ethanol) were isolated.

Workup

  1. temperaturewhile heating
  2. customrising above 5° C. during this operation
  3. additionafter which the reaction mixture was poured onto ice water
  4. filtrationThe precipitate was filtered off under suction
  5. washwashed thoroughly with water

Sources & evidence

ORD record
ord-fae1199e07534854a328a17294b75794
Source dataset
uspto-grants-1986_03
Patent number
US04575508

Reaction notes

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