2-Naphthol → 1-(beta-Naphthoxy)-2-benzyloxy-3-(iso-propylamino)-propane

HRID 328898Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[CH:12]([N:15]1[CH2:18][CH:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16]1)([CH3:14])[CH3:13].[OH-].[K+]>CCOCC>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:18][CH:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:16][NH:15][CH:12]([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 17.3 parts of β-naphthol, 20.5 parts of 1-(iso-propyl)-3-benzyloxyazetidine, and 1.1 parts of potassium hydroxide was heated under nitrogen gas at 180° C. for 8 hours with agitation. The reaction mixture was cooled and dissolved in 100 parts of ether. The solution was washed with 50 parts of 2N-sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate. Ether was distilled off and the residue was subjected to distillation to yield 29.3 parts of 1-(β-naphthoxy)-2-benzyloxy-3-(iso-propylamino)propane boiling at 185° -190° C. under 1 mm Hg. The yield was 84%. The results of infra-red spectrum analysis and nuclear magnetic resonance analysis of the product are as follows:

Workup

temperatureThe reaction mixture was cooled
washThe solution was washed with 50 parts of 2N-sodium hydroxide aqueous solution
dry with materialdried over anhydrous sodium sulfate
distillationEther was distilled off
distillationthe residue was subjected to distillation

Sources & evidence

ORD record: ord-2f48bb655e6745d28b97b9dbbda54b93
Source dataset: uspto-grants-1977_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04018824

Reaction notes

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