1-Naphthol → 1-(alpha-Naphthoxy)-2-benzyloxy-3-(iso-propylamino)-propane
Reaction equation
[CH:1]([N:4]1[CH2:7][CH:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5]1)([CH3:3])[CH3:2].[C:16]1([OH:26])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>CCOCC>[C:16]1([O:26][CH2:5][CH:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][NH:4][CH:1]([CH3:2])[CH3:3])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
To a mixture of 6.2 parts of 1-(iso-propyl)-3-benzyloxyazetidine and 43 parts of α-naphthol 1.5 parts of sodium hydroxide was added, and the mixture was heated at 200° C. for 16 hours. The reaction mixture was cooled, and 100 parts of ether were added thereto. Excessive α-naphthol was removed by extraction with 2N-sodium hydroxide aqueous solution. The remaining ether layr was washed in water and dried over anhydrous sodium sulfate. After distillation of ether, the residue was subjected to distillation to yield 8.3 parts of 1-(α-naphthoxy)-2-benzyloxy-3-(iso-propylamino)-propane boiling at 192°-195° C. The yield was 79%.
Workup
- additionwas added
- temperatureThe reaction mixture was cooled
- customExcessive α-naphthol was removed by extraction with 2N-sodium hydroxide aqueous solution
- washThe remaining ether layr was washed in water
- dry with materialdried over anhydrous sodium sulfate
- distillationAfter distillation of ether
- distillationthe residue was subjected to distillation
Sources & evidence
- ORD record
- ord-08d8eafb95d447d1a0a5fec4a5d9df11
- Source dataset
- uspto-grants-1977_04
- Patent number
- US04018824
Reaction notes
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