Melatonin → HCID 24750193, compound

HRID 1631204Notes

Reaction equation

[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.Br[CH2:12]CC#N.C(#N)CC.[CH3:20][C:21]([NH:23][CH2:24][CH2:25]C1C2C=C(OC)C=CC=2NC=1)=[O:22]>>[CH3:10][O:9][C:5]1[CH:4]=[C:3]([N:2]([CH3:12])[CH2:1][CH2:25][CH2:24][NH:23][C:21](=[O:22])[CH3:20])[CH:8]=[CH:7][CH:6]=1

Participants

Reactant 4

HCID 896Melatonin

HCID 7854Propionitrile

HCID 170203-Bromopropionitrile

HCID 84349N-Methyl-m-anisidine

Product 1

HCID 24750193HCID 24750193, compound

Procedure

N-cyanoalkylation of N-methyl-3-methoxyaniline (3j) with 3-bromopropionitrile, followed by hydrogenation and N-acetylation of the intermediate propionitrile 4m [Yield (4m): 88%; oil; 1H-NMR (CDCl3): δ 2.57 (t, 2H), 3.02 (s, 3H), 3.70 (t, 2H), 3.80 (s, 3H), 6.25 (t, 1H), 6.31-6.38 (m, 2H), 7.18 (t, 1H)], according to the procedure previously described for the preparation of 5a, provided the title compound 5m. Yield (5m): 52%; oil. 1H-NMR (CDCl3): δ 1.80 (m, 2H), 1.95 (s, 3H), 2.91 (s, 3H), 3.24-3.40 (m, 4H), 3.80 (s, 3H), 5.60 (brs, 1H), 6.24-6.37 (m, 3H), 7.15 (t, 1H).

Sources & evidence

ORD record: ord-1ee38d8f05d144eb875257a9abc460f2
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791163B2

Reaction notes

Loading…