Dimethylamine, hydrochloride → (+/-)-trans-2-Dimethylamino-6-propyl-5,5a,6,7,8, 9,9a, 10-octahydropyrido [2,3-g]quinoline
Reaction equation
Cl.Cl[C:3]1[CH:4]=[CH:5][C:6]2[CH2:15][C@H:14]3[C@@H:9]([CH2:10][CH2:11][CH2:12][N:13]3[CH2:16][CH2:17][CH3:18])[CH2:8][C:7]=2[N:19]=1.Cl.[CH3:21][NH:22][CH3:23].[OH-].[Na+]>O>[CH3:21][N:22]([CH3:23])[C:3]1[CH:4]=[CH:5][C:6]2[CH2:15][C@H:14]3[C@@H:9]([CH2:10][CH2:11][CH2:12][N:13]3[CH2:16][CH2:17][CH3:18])[CH2:8][C:7]=2[N:19]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
A mixture of (±)-trans-2-chloro-6-propyl-5,5a,6,7,8,9,9a,10-octahydropyrido[2,3-g]quinoline hydrochloride (1.00 g, 3.32 mmol) and dimethylamine hydrochloride (15 g) was heated to 200° C. to form a homogeneous molten semi-solid. After 30 minutes, the molten semi-solid was poured into water, made basic with dilute NaOH solution, and extracted with methylene chloride. The extract was dried (Na2SO4) and concentrated to give the crude product as a brown solid. Purification by flash chromatography (10% methanol in methylene chloride, NH4OH) provided (±)-trans-2-dimethylamino-6-propyl-5,5a,6,7,8, 9,9a,10-octahydropyrido[2,3-g]quinoline (Rf =0.54, 568 mg, 63% yield) as an orange oil.
Workup
- customto form a homogeneous molten semi-solid
- extractionextracted with methylene chloride
- dry with materialThe extract was dried (Na2SO4)
- concentrationconcentrated
- customto give the crude product as a brown solid
- customPurification by flash chromatography (10% methanol in methylene chloride, NH4OH)
Sources & evidence
- ORD record
- ord-19d6ec18c4c245d592b116ea6e177b89
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04977149
Reaction notes
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