Dichloromethane → N-[2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl]benzamide hydrochloride

HRID 1356279Notes

Reaction equation

HRID 1356279 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][N:12]1[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]2[CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH2:25][C:13]1=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C(O)=O)(F)(F)F.C(Cl)[Cl:41]>>[ClH:41].[CH2:21]1[C:14]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[N:12]([CH2:11][CH2:10][NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:13]=2[CH2:25][CH2:24][NH:23][CH2:22]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 22396732tert-butyl 6-[2-(benzoylamino)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

Product 1

HCID 22396552N-[2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl]benzamide hydrochlorideYield 79%

Procedure

tert-Butyl 6-[2-(benzoylamino)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.0398 g, 0.0918 mmol) was dissolved in CH2Cl2 (2 mL) at rt. CF3CO2H (1 mL) was added, then the reaction mixture was stirred for 2 h. The reaction mixture was concentrated and the residue was taken up in EtOAc (2 mL). HCl (1N) in Et2O (2 mL) was added and the precipitated salt was collected by filtration. N-[2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl]benzamide hydrochloride (0.0271 g) was obtained in 79% yield. 1H NMR (300 MHz, CD3OD) δ 3.18-3.21, 3.33-3.38, 3.42-3.49, 3.69, 4.44, 7.05, 7.15, 7.38-7.54, 7.60, 7.60, 8.55-8.59; MS (ESI+) for C21H23N3O m/z 334.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionHCl (1N) in Et2O (2 mL) was added
  3. filtrationthe precipitated salt was collected by filtration

Sources & evidence

ORD record
ord-4819e109f4504e3d9a43a6086d39f09b
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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