Melatonin → HCID 24750070, compound

HRID 1631203Notes

Reaction equation

HRID 1631203 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].ClCC#N.[CH3:14][C:15]([NH:17][CH2:18][CH2:19]C1C2C=C(OC)C=CC=2NC=1)=[O:16]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][CH2:19][CH2:18][NH:17][C:15](=[O:16])[CH3:14])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 896MelatoninHCID 7856ChloroacetonitrileHCID 108243-Methoxyaniline

Product 1

HCID 24750070HCID 24750070, compound

Procedure

N-cyanoalkylation of 3-methoxyaniline (3l) using chloroacetonitrile, followed by hydrogenation and N-acetylation of the intermediate nitrile 4l [Yield (4l): 58%; 1H-NMR (CDCl3): δ 3.80 (s, 3H), 4.05 (s, 2H), 6.25-6.48 (m, 2H), 7.18 (t, 1H)], according to the procedure previously described for the preparation of 5a, provided the title compound 5l; oil. 1H-NMR (CDCl3): δ 2.00 (s, 3H), 3.27 (m, 2H), 3.53 (m, 2H9, 3.78 (s, 3H), 5.84 (brs, 1H), 6.17-6.32 (m, 3H), 7.09 (t, 1H).

Sources & evidence

ORD record
ord-dbc65fc68a104d1ebdbbe12b993ce234
Source dataset
uspto-grants-2014_07
Patent number
US08791163B2

Reaction notes

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