Chloroacetonitrile → 2-[[2-(6-methoxy-1H-indol-3-yl)-ethyl]-amino]-acetonitrile

HRID 476878

Reaction equation

HRID 476878 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:12](=[CH:13][CH:14]=1)[C:8]([CH2:9][CH2:10][NH2:11])=[CH:7][NH:6]2.[CH2:15]([N:17](CC)CC)[CH3:16].ClCC#N>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:12]([C:8]([CH2:9][CH2:10][NH:11][CH2:16][C:15]#[N:17])=[CH:7][NH:6]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 176542-(2-Aminoethyl)-5-methoxyindole

Product 1

HCID 198370192-[[2-(6-methoxy-1H-indol-3-yl)-ethyl]-amino]-acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

28.5 g of 6-methoxytryptamine were refluxed in 300 ml of tetrahydrofuran in the presence of 42 ml of triethylamine and 11.4 ml of chloroacetonitrile were added over 2 hours. The heating was continued for 1 hour and after allowing the temperature to return to the ambient, the precipitate was eliminated by filtration. The filtrate was concentrated to dryness under reduced pressure and the residue was taken up in ethyl acetate, washed with water, dried and the solvent was eliminated under reduced pressure to obtain 17.9 g of the expected product melting at approx. 80° C.

Workup

  1. additionwere added over 2 hours
  2. filtrationthe precipitate was eliminated by filtration
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b6a94d5dd8734371acbf505ffefe1648
Source dataset
uspto-grants-1989_12
Patent number
US04886802

Linked notes

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