8,9-Dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole → HCID 59075499, compound

HRID 2307047Notes

Reaction equation

HRID 2307047 reaction equation
[Cl:1][C:2]1[C:3]([Cl:16])=[CH:4][C:5]2[C:6]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][C:7]=3[NH:8][C:9]=2[CH:10]=1>C(O)(C(F)(F)F)=O.CO>[Cl:1][C:2]1[C:3]([Cl:16])=[CH:4][C:5]2[C@@H:6]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][C@@H:7]3[NH:8][C:9]=2[CH:10]=1

Participants

4

Reactant 1

HCID 226092048,9-Dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

Product 1

HCID 59075499HCID 59075499, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 8,9-dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.40 g, 1.6 mmol) in TFA (4.0 mL) was cooled to 0° C., then a freshly prepared solution of Na(CN)BH3 (0.49 g, 7.8 mmol) in MeOH (.1.5 mL) was added dropwise. The ice bath was removed after the addition was complete. After 2.5 h, the reaction was diluted with H2O, made basic with 50% aqueous NaOH, and extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography and prep HPLC to give 0.14 g (36%) of the title compound as pale orange solid. 1H NMR (d-CHCl3) δ 7.00, 6.58, 4.22, 3.81, 3.58, 3.14-2.98, 2.79, 2.07-1.87: IR (drift) 3201, 3170, 3149, 3031, 2927, 2852, 2838, 2750, 1608, 1483, 1450, 1365, 1273, 832, 660 cm−1; HRMS (FAB) calcd for C12H14Cl2N2+H 257.0612, found 257.0614.

Workup

  1. customThe ice bath was removed
  2. additionafter the addition
  3. additionthe reaction was diluted with H2O
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by silica gel chromatography and prep HPLC

Sources & evidence

ORD record
ord-d96d008378ad4fc59fbfa4bb328378ff
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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