Dicyclohexylcarbodiimide → HCID 4004276, compound

HRID 1451653Notes

Reaction equation

HRID 1451653 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH:7]=[CH:8][C:9]([OH:11])=O)([O-:3])=[O:2].ON1C2C=CC=CC=2N=N1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][C:36]=1[O:37][CH3:38])[CH2:33][NH:32][CH2:31][CH2:30]2.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][C:36]=1[O:37][CH3:38])[CH2:33][N:32]([C:9](=[O:11])[CH:8]=[CH:7][C:6]1[CH:12]=[CH:13][CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH2:31][CH2:30]2

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 156236,7-Dimethoxy-1,2,3,4-TetrahydroisoquinolineHCID 683902-Propenoic acid, 3-(3-nitrophenyl)-HCID 757711-Hydroxybenzotriazole

Product 1

HCID 4004276HCID 4004276, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-nitrocinnamic acid (10 g) and 1-hydroxybenzotriazole (8.2 g) in DMF (100 ml) was stirred at room temperature for 10 min. 1,2,3,4-Tetrahydro-6,7-dimethoxy-isoquinoline (10 g) was then added, followed by dicyclohexylcarbodiimide (10.6 g) and the mixture was stirred at 50° for 48 h and then filtered. The filtrate was concentrated in vacuo, treated with dilute sodium hydroxide and extracted with dichloromethane. The dried organic extract was evaporated and purified by column chromatography eluting with dichloromethane/methanol (97:3) to give the title compound (7.8 g). NMR includes a signal at d 3.85 (6H,s,OCH3).

Workup

  1. stirringthe mixture was stirred at 50° for 48 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiontreated with dilute sodium hydroxide
  5. extractionextracted with dichloromethane
  6. extractionThe dried organic extract
  7. customwas evaporated
  8. custompurified by column chromatography
  9. washeluting with dichloromethane/methanol (97:3)

Sources & evidence

ORD record
ord-058b11cc72e04aaf9470468c39b70446
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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