Dichloromethane → 2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethanamine dihydrochloride

HRID 1356275Notes

Reaction equation

HRID 1356275 reaction equation
[NH2:1][CH2:2][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.C(Cl)[Cl:33]>>[ClH:33].[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][CH2:2][NH2:1])[C:5]=2[CH2:17][CH2:16][NH:15][CH2:14]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 22396663tert-butyl 6-(2-aminoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

Product 1

HCID 223967722-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethanamine dihydrochloride

Procedure

tert-Butyl 6-(2-aminoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.0336 g, 0.102 mmol) was dissolved in CH2Cl2 (2 mL) at rt. CF3CO2H (1 mL) was added and the reaction mixture was stirred for 4 h. The reaction mixture was concentrated and the residue was taken up in EtOAc (2 mL). HCl in Et2O (1 N) and MeOH were added and the mixture was concentrated to give crude 2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethanamine dihydrochloride (0.0339 g). 1H NMR (300 MHz, DMF-d7) δ 3.48-3.51, 3.53-3.59, 3.65-3.70, 3.75-3.79, 4.94, 7.27, 7.35, 7.72, 7.91; MS (ESI+) for C14H19N3 m/z 230.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionHCl in Et2O (1 N) and MeOH were added
  3. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-99b23abc49304b5abc1811f2dca18bd8
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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