Ammonia → HCID 178483704, compound

HRID 1922367Notes

Reaction equation

HRID 1922367 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([NH2:15])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.I.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](SC)=[NH:24].N>CCO.CO>[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:23]([C:19]3[S:18][CH:22]=[CH:21][CH:20]=3)=[NH:24])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 28419064HCID 28419064, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178483704HCID 178483704, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 1-(2-(dimethylamino)ethyl)-1,2,3,4-tetrahydroquinolin-6-amine (900 mg, 4.10 mmol) in 25 mL EtOH was treated with methyl thiophene-2-carbimidothioate hydroiodide (2.34 g, 1.43 mmol) and stirred overnight at room temperature. Argon was bubbled through the mixture for 20 minutes then it was partitioned between CH2Cl2 (100 mL) and saturated sodium bicarbonate (20 mL). The organic layer was separated and the aqueous layer was extracted with an additional 50 mL CH2Cl2. The combined organic layers were rinsed with water, dried over sodium sulfate, filtered and concentrated to give a dark oil which was subjected to flash chromatography on silica gel using 5% MeOH/CH2CH2then 5% 2M NH3 in MeOH/CH2C12 to give an orange solid. 1H-NMR (DMSO-d6) δ: 7.66 (d, J=3.6 Hz, 1H), 7.55 (d, J=4.8 Hz, 1H), 7.08-7.05 (m, 1H), 6.57-6.48 (m, 3H), 6.25 (brs, 2H), 3.29-3.21 (m, 4H), 2.65 (t, J=6.3 Hz, 2H), 2.39 (t, J=6.3 Hz, 2H), 2.19 (s, 6H), 1.85-1.82 (m, 2H).

Workup

  1. customArgon was bubbled through the mixture for 20 minutes
  2. customit was partitioned between CH2Cl2 (100 mL) and saturated sodium bicarbonate (20 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with an additional 50 mL CH2Cl2
  5. washThe combined organic layers were rinsed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a dark oil which
  10. customto give an orange solid

Sources & evidence

ORD record
ord-56dc1e8f9c1145bfade7d9be2988fb23
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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