N-(3-Hydroxy-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c][7]annulen-5-yl)ethanimidic acid → HCID 21893894, compound

HRID 720930Notes

Reaction equation

HRID 720930 reaction equation
[CH3:1][C:2]([NH:4][C@@H:5]1[C:15]2[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]=2[C:13]2[C:8](=[CH:9][C:10]([O:25][CH3:26])=[C:11]([O:23][CH3:24])[C:12]=2[O:21][CH3:22])[CH2:7][CH2:6]1)=[O:3].[C:27](Cl)(=[O:29])[NH2:28].[N:31]1([CH:37]2[CH2:42][CH2:41]N[CH2:39][CH2:38]2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>N1C=CC=CC=1>[N:31]1([CH:37]2[CH2:42][CH2:41][N:28]([C:27]([O:20][C:17]3[CH:18]=[CH:19][C:14]4[C:13]5[C:12]([O:21][CH3:22])=[C:11]([O:23][CH3:24])[C:10]([O:25][CH3:26])=[CH:9][C:8]=5[CH2:7][CH2:6][CH:5]([NH:4][C:2](=[O:3])[CH3:1])[C:15]=4[CH:16]=3)=[O:29])[CH2:39][CH2:38]2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 242436N-(3-Hydroxy-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c][7]annulen-5-yl)ethanimidic acidHCID 21893904HCID 21893904, compound

Product 1

HCID 21893894HCID 21893894, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of N-acetyl-colchinol (300 mg, 0.84 mmol), (J. Cech F. Santacy Collect. Czech Comm 1949, 4, 532–539), in pyridine (5 ml) was treated with 4-piperidinopiperidine carbamoyl chloride (346 mg, 1.5 mmol), (K. H. Henegar et al. J. Org. Chem., 1997, 62, 6588–6597) and the solution heated at reflux for 1 hour. The cooled mixture was filtered and the filtrate concentrated under reduced pressure. The residue was purified on silica gel eluting with methanol to give the title compound (180 mg) as a white solid.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe cooled mixture was filtered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified on silica gel eluting with methanol

Sources & evidence

ORD record
ord-3eba5fd1af694dc0830636eca601bc41
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Reaction notes

Loading…