Dichloromethane → HCID 22396573, compound

HRID 1370472Notes

Reaction equation

HRID 1370472 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:10]2[C:11]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18][C:12]=3[NH:13][C:14]=2[CH:15]=[CH:16][CH:17]=1.C(Cl)Cl>C(C(O)=O)(F)(F)F>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[C:10]2[C:11]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18][C:12]=3[NH:13][C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 22396577HCID 22396577, compound

Product 1

HCID 22396573HCID 22396573, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 10-(2,6-difluorophenyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.700 g, 1.76 mmol) was dissolved in CF3CO2H (4 mL) and CH2Cl2 (14 mL) and the reaction mixture was stirred at rt for 3 h. The reaction mixture was cooled in an ice bath and quenched with cold 1N NaOH (100 mL). The resulting mixture was extracted with 3% CH3OH in CH2Cl2 (3×50 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated. The crude product (0.51 g) was chromatographed (SiO2 30 g, eluted with 90:10:1 CH2Cl2:CH3OH:conc. NH4OH) to yield 10-(2,6-difluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.458 g) in 87% yield. 1H NMR (400 MHz, Acetone-d6) δ 2.35-2.38, 2.74-2.77, 2.95-2.98, 6.84, 7.08, 7.12, 7.36, 7.50; MS (ESI+) for C18H16F2N2 m/z 299.1 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customquenched with cold 1N NaOH (100 mL)
  3. extractionThe resulting mixture was extracted with 3% CH3OH in CH2Cl2 (3×50 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product (0.51 g) was chromatographed
  8. wash(SiO2 30 g, eluted with 90:10:1 CH2Cl2:CH3OH:conc. NH4OH)

Sources & evidence

ORD record
ord-9eee4bbc6e5c4f3a86bf01a325b11014
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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