1-(2-Morpholinoethyl)-1,2,3,4-tetrahydroquinolin-6-amine → HCID 178511877, compound

HRID 1922503Notes

Reaction equation

HRID 1922503 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]2[C:18]3[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10]2)[CH2:3][CH2:2]1.I.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](SC)=[NH:27]>C(O)C.C(=O)(O)[O-].[Na+]>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]2[C:18]3[C:13](=[CH:14][C:15]([NH:19][C:26]([C:22]4[S:21][CH:25]=[CH:24][CH:23]=4)=[NH:27])=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 284191151-(2-Morpholinoethyl)-1,2,3,4-tetrahydroquinolin-6-amineHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178511877HCID 178511877, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of compound 4 (0.23 g, 0.88 mmol) in dry ethanol (20 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.502 g, 1.76 mmol) at room temperature and was stirred for 3 hours. The mixture was diluted with saturated sodium bicarbonate solution (50 mL) and was extracted with CH2Cl2 (100 mL). The organic layer was washed with brine (20 mL) and dried (Na2SO4). The concentrated crude product was subject to flash chromatography on silica gel using 5% methanol/CH2Cl2, which resulted in a brown foam, compound 64 (0.194 g, 59%). 1H NMR (CDCl3) δ 7.66 (d, J=3.9 Hz, 1H), 7.54 (d, J=4.5 Hz, 1H), 7.06 (dd, J=3.6, 5.1 Hz, 1H), 6.53 (s, 2H), 6.46 (s, 1H), 6.21 (brs, 2H), 3.57 (t, J=9.3 Hz, 4H), 3.24 (t, J=11.4 Hz, 2H), 3.65 (t, J=12.6 Hz, 2H), 2.45-2.41 (m, 6H), 1.88-1.80 (m, 2H); MS-ESI (m/z, %): 372 (11), 371 (MH+, 100), 258 (9); ESI-HRMS calculated for C20H27N4OS (MH+): Calculated: 371.1914, Observed: 371.1900.

Workup

  1. extractionwas extracted with CH2Cl2 (100 mL)
  2. washThe organic layer was washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationThe concentrated crude product

Sources & evidence

ORD record
ord-1224b01834274fbfa54e08de4ace1b8b
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…