Chloroacetonitrile → HCID 19837048, compound

HRID 476876Notes

Reaction equation

HRID 476876 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:11](=[CH:12][CH:13]=1)[C:7]([CH2:8][CH2:9][NH2:10])=[CH:6][NH:5]2.Cl[CH2:15][C:16]#[N:17]>O1CCCC1.C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]2[C:11]([C:7]([CH2:8][CH2:9][NH:10][CH2:15][C:16]#[N:17])=[CH:6][NH:5]2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 7856ChloroacetonitrileHCID 1900062-(6-Methyl-1H-indol-3-yl)ethan-1-amine

Product 1

HCID 19837048HCID 19837048, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

17 g of 6-methyltryptamine were dissolved at 40° C. under inert atmosphere in 500 ml of tetrahydrofuran, and the solution was allowed to return to ambient temperature. 14.6 ml of 1,5-diaza[5,4,0]undec-5-ene were added followed by 6.2 ml of chloroacetonitrile and stirring for 15 hours. The solvent was eliminated under reduced pressure and the residue was taken up in 250 ml of methylene chloride, washed with water, dried and concentrated to dryness. The 25 g of crude product was purified by chromatography on silica (eluent: methylene chloride-ethyl acetate 3-7) to obtain 13.2 g of the expected product melting at 92° C.

Workup

  1. customto return to ambient temperature
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated to dryness
  5. customThe 25 g of crude product was purified by chromatography on silica (eluent: methylene chloride-ethyl acetate 3-7)

Sources & evidence

ORD record
ord-18c2620c8e904afd9387c033a505751a
Source dataset
uspto-grants-1989_12
Patent number
US04886802

Reaction notes

Loading…