Melatonin → HCID 24750191, compound

HRID 1631202Notes

Reaction equation

HRID 1631202 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:15][C:16]([NH:18][CH2:19][CH2:20]C1C2C=C(OC)C=CC=2NC=1)=[O:17]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([N:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:20][CH2:19][NH:18][C:16](=[O:17])[CH3:15])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 896MelatoninHCID 149586063-Bromo-N-phenylaniline

Product 1

HCID 24750191HCID 24750191, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of nitrile 4f (1.16 mmol), prepared according to the method previously described for the preparation of 4a, but starting with N-(3-bromophenyl)-aniline (3f) [yield (4f): 37%; oil; 1H-NMR (CDCl3): δ 4.50 (s, 2H), 6.87 (m, 1H), 7.08-7.46 (m, 8H)] in dry THF (6 mL), was hydrogenated according to the procedure previously described for the preparation of 5a to provide the title compound 5f. The crude product was purified by flash-chromatography on silica gel (dichloromethane/acetone, 95:5 as eluent). Yield (5f): 20%; 1H-NMR (CDCl3): δ 1.90 (s, 3H), 3.48 (m, 2H), 3.85 (m, 2H), 6.03 (brs, 1H), 6.81-7.41 (m, 9H).

Sources & evidence

ORD record
ord-70f75690dfbf45769790b8585ca53597
Source dataset
uspto-grants-2014_07
Patent number
US08791163B2

Reaction notes

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