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

HRID 2306965Notes

Reaction equation

HRID 2306965 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-085feec253744a3ab532662acf9866b5
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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