Chloroform → HCID 1548084, compound

HRID 1371910Notes

Reaction equation

HRID 1371910 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:21]=[C:20]2[C:13]([NH:14][CH:15]=[C:16]2[CH2:17][CH2:18][NH2:19])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:22]1(=O)[O:27][C:25](=[O:26])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.C(N(CC)C(C)C)(C)C.C(Cl)(Cl)Cl>N1C=CC=CC=1>[CH2:2]([O:9][C:10]1[CH:21]=[C:20]2[C:13](=[CH:12][CH:11]=1)[NH:14][CH:15]=[C:16]2[CH2:17][CH2:18][N:19]1[C:25](=[O:26])[C:24]2[C:23](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:22]1=[O:27])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6811Phthalic AnhydrideHCID 81531DiisopropylethylamineHCID 282878552055-23-9

Product 1

HCID 1548084HCID 1548084, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Combine 5-benzyloxytryptamine hydrochloride (1 g, 3.3 mmol), phthalic anhydride (.56 g, 4.0 mmol) and N,N-diisopropylethylamine (0.86 g, 6.6 mmol) in 25 mL anhydrous pyridine and reflux for 1 hour, cool to room temperature and treat with 4 g 3 Å molecular sieves. Refluxing was continued for 60 hours then the mixture was filtered. Concentrate under vacuum to give a residue which is mixed with 25 mL CHCl3 and filtered to give a solid. Purification of the filtrate by chromatography on silica gel eluting with 1% MeOH in CHCl3 to give an additional amount of title compound: ISMS 397 (M+1); Analysis for C25H20N2O3 0.3H2O C7H8: calcd: C, 75.09; H, 5.25; N, 6.82; found: C, 75.00; H, 5.22; N, 6.96.

Workup

  1. additiontreat with 4 g 3 Å molecular sieves
  2. temperatureRefluxing
  3. filtrationthe mixture was filtered
  4. concentrationConcentrate under vacuum
  5. customto give a residue which
  6. filtrationfiltered
  7. customto give a solid
  8. customPurification of the filtrate by chromatography on silica gel eluting with 1% MeOH in CHCl3

Sources & evidence

ORD record
ord-ad70cbd4d8a648d39dc39f741617675d
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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