N-Carbethoxyphthalimide → HCID 1548084, compound

HRID 1292384Notes

Reaction equation

HRID 1292384 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(N1[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]2[C:28]1=[O:37])(OCC)=O>C(N(CC)CC)C>[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:31](=[O:32])[C:30]2[C:29](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:28]1=[O:37])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 282878552055-23-9

Product 1

HCID 1548084HCID 1548084, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred suspension of 5-benzyloxytryptamine hydrochloride (1.0 g in 10 mL of dry tetrahydrofuran) was added triethylamine (0.50 mL) followed by N-carbethoxyphthalimide (750 mg) and the mixture heated to reflux on an oil bath. After 48 hours the reaction was cooled to room temperature, filtered and the filtrate concentrated in vacuo. The resulting solid was suspended in a mixture of hexane/methylene chloride (2.5:1, 50 mL) and filtered to give the title compound (1.3 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. additionThe resulting solid was suspended in a mixture of hexane/methylene chloride (2.5:1, 50 mL)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b7d2523903034de8b9664e0178808d24
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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