Isopropanol → HCID 18651838, compound
Reaction equation
Cl.[CH3:2][C@@H:3]1[CH2:8][CH2:7][C@@H:6]([CH:9]([CH3:11])[CH3:10])[C@H:5]([O:12][CH2:13][CH2:14][N:15]([CH2:17][CH2:18]Cl)[CH3:16])[CH2:4]1.C(O)(C)C.[CH:24]([NH2:27])([CH3:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:2][C@@H:3]1[CH2:8][CH2:7][C@@H:6]([CH:9]([CH3:11])[CH3:10])[C@H:5]([O:12][CH2:13][CH2:14][N:15]([CH2:17][CH2:18][NH:27][CH:24]([CH3:26])[CH3:25])[CH3:16])[CH2:4]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
5 g of N-[2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)ethyl]-N-(2-chloro ethyl)-N-methylamine hydrochloride were added to a mixture of 50 ml isopropanol and 50 ml water. 1.9 g of isopropylamine and 7.7 g of potassium carbonate were then added, and the reaction mixture was heated under reflux for 5 hours. The reaction mixture was worked up by diluting it with 100 ml of water and extracting the solution with ethyl acetate. The organic phase was worked up as described in Example 1 C). 4.78 g of N-[2-((1R,3R,4S)-1-methyl-4-isopropylcyclo hex-3-yloxy)ethyl]-N-[2-(isopropylamino)ethyl]-N-methylamine were obtained. The free base was then converted into the corresponding hydrochloride analogously to Example 1 D). 5.1 g of N-[2-((1R,3R,4S)-1-methyl-4-isopropylcycl ohex-3-yloxy)ethyl]-N-[2-(isopropylamino)ethyl]-N-methylamine dihydrochloride having a melting point of 156° C.-158° C. were obtained.
Workup
- temperaturethe reaction mixture was heated
- temperatureunder reflux for 5 hours
- extractionextracting the solution with ethyl acetate
Sources & evidence
- ORD record
- ord-10b6e182110646048ed7b9fb3d734569
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05212173
Reaction notes
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