Ammonia → 2-Chloro-5,6,7,8,9,10-hexahydrocyclohepta(b)indole-6-carboxamide

HRID 450833Notes

Reaction equation

HRID 450833 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH:11]([C:16]([O:18]C)=O)[CH2:12][CH2:13][CH2:14][CH2:15][C:5]2=1.[NH3:20]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH:11]([C:16]([NH2:20])=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][C:5]2=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 117018402-Chloro-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole-6-carboxylic acid methyl ester

Product 1

HCID 36120162-Chloro-5,6,7,8,9,10-hexahydrocyclohepta(b)indole-6-carboxamideYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxylate (10 g, 36 mmol) was dissolved in 7 N ammonia in methanol (350 mL) and transferred to Parr pressure reactor. The reaction vessel was purged briefly to displace any air with Nitrogen. The reaction was then heated to 90° C. for 48 h. The reaction was cooled to r.t. and the solvent removed in vacuo, the crude residue was applied to a Biotage and eluted with grading (1/1 heptane/ethyl acetate to 0/1 heptane/ethyl acetate) to afford product as an off white foam, which was triturated with DCM to afford pure product 2 g (21%) as an off white solid.

Workup

  1. customThe reaction vessel was purged briefly
  2. temperatureThe reaction was cooled to r.t.
  3. customthe solvent removed in vacuo
  4. washeluted with grading (1/1 heptane/ethyl acetate to 0/1 heptane/ethyl acetate)
  5. customto afford product as an off white foam, which
  6. customwas triturated with DCM

Sources & evidence

ORD record
ord-b35793a36b81454290587501a6c320c8
Source dataset
uspto-grants-2013_07
Patent number
US08486990B2

Reaction notes

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