Hydrochloric Acid → 2-(2,3,4,5-Tetrahydroazepino[4,5-b]indol-6(1h)-yl)acetamide hydrochloride

HRID 1370387Notes

Reaction equation

HRID 1370387 reaction equation
[NH2:1][C:2](=[O:25])[CH2:3][N:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:6]2[CH2:13][CH2:14][N:15](C(OC(C)(C)C)=O)[CH2:16][CH2:17][C:5]1=2.C(C(O)=O)(F)(F)F.[ClH:33]>C(Cl)Cl.CCOC(C)=O.CCOCC>[ClH:33].[CH2:13]1[C:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[N:4]([CH2:3][C:2]([NH2:1])=[O:25])[C:5]=2[CH2:17][CH2:16][NH:15][CH2:14]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 22396556tert-butyl 6-(2-amino-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

Product 1

HCID 223967072-(2,3,4,5-Tetrahydroazepino[4,5-b]indol-6(1h)-yl)acetamide hydrochlorideYield 80%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 6-(2-amino-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.0233 g, 0.0678 mmol) was dissolved in CH2Cl2 (2 mL) at rt. CF3CO2H (0.8 mL) was added, then the reaction mixture was stirred for 30 min. The reaction mixture was concentrated to give a crude product (0.0288 g). The crude product was dissolved in EtOAc (1 mL), 1 N HCl in Et2O (2 mL) was added, and the precipitated salt was collected by filtration. 2-(2,3,4,5-Tetrahydroazepino[4,5-b]indol-6(1H)-yl)acetamide hydrochloride (0.0151 g) was obtained in 80% yield. 1H NMR (300 MHz, DMF-d7) δ 3.29-3.33, 3.40-3.43, 3.50-3.58, 4.97, 7.07, 7.15, 7.45, 7.53; MS (ESI+) for C14H17N3O m/z 244.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a crude product (0.0288 g)
  3. filtrationthe precipitated salt was collected by filtration

Sources & evidence

ORD record
ord-9eba8c1542a849718c87a0a6ad5ce0c8
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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