Maleic Acid → HCID 69795345, compound

HRID 1370376Notes

Reaction equation

HRID 1370376 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=1)[O:6][CH2:7][CH2:8][N:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[CH2:18][CH2:19][N:20](C(OC(C)(C)C)=O)[CH2:21][CH2:22][C:10]1=2.[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37]>Cl.CO>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=1)[O:6][CH2:7][CH2:8][N:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][C:10]1=2

Participants

5

Reactant 2

HCID 444266Maleic AcidHCID 22396771HCID 22396771, compound

Product 1

HCID 69795345HCID 69795345, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl 6-[2-(3-methoxyphenoxy)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.447 g, 1.02 mmol) in methanolic hydrochloric acid was warmed in a 50° C. bath for 1.5 h. The mixture was evaporated, taken up in ethyl acetate, then washed with 1 N sodium hydroxide. The organic phase was dried and evaporated to provide an oil. The oil was diluted with methanol and a solution of maleic acid in methanol was added. Evaporation and crystallization of the residue from methanol, ethyl acetate, and hexanes, afforded 0.347 g of the title compound (mp=131-133° C.).

Workup

  1. customThe mixture was evaporated
  2. washwashed with 1 N sodium hydroxide
  3. customThe organic phase was dried
  4. customevaporated
  5. customto provide an oil
  6. customEvaporation and crystallization of the residue from methanol, ethyl acetate, and hexanes

Sources & evidence

ORD record
ord-40c4229a86ba42a1a9b11420ed2618d8
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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