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

HRID 1370400Notes

Reaction equation

HRID 1370400 reaction equation
[NH:1]([C:8]([NH:10][CH2:11][CH2:12][N:13]1[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[CH2:22][CH2:23][N:24](C(OC(C)(C)C)=O)[CH2:25][CH2:26][C:14]1=2)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C(O)=O)(F)(F)F.C(Cl)[Cl:42]>>[ClH:42].[C:2]1([NH:1][C:8]([NH:10][CH2:11][CH2:12][N:13]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15]3[CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:14]2=3)=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 22396805tert-butyl 6-{2-[(anilinocarbonyl)amino]ethyl}-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

Product 1

HCID 22396703N-Phenyl-N'-[2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl]urea hydrochlorideYield 88%

Procedure

tert-Butyl 6-{2-[(anilinocarbonyl)amino]ethyl}-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.0390 g, 0.0869 mmol) was dissolved in CH2Cl2 (2 mL) at rt. CF3CO2H (1 mL) was added, then the reaction mixture was stirred for 45 min. The reaction mixture was concentrated and the residue was taken up in EtOAc (2 mL). 1 N HCl in Et2O (2 mL) was added and the precipitated salt was collected by filtration. N-Phenyl-N′-[2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl]urea hydrochloride (0.0296 g) was obtained in 88% yield. 1H NMR (300 MHz, CD3OD) δ 3.19-3.22, 3.35-3.38, 3.43-3.53, 4.35, 6.97-7.03, 7.07, 7.17, 7.25-7.27, 7.44, 7.48; MS (ESI+) for C21H24N4O m/z 349.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition1 N HCl in Et2O (2 mL) was added
  3. filtrationthe precipitated salt was collected by filtration

Sources & evidence

ORD record
ord-28129294f59a417da54fc9fdbf9d74b1
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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