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

HRID 2198845Notes

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]=1

Participants

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 2 N-sodium hydroxide aqueous solution. The remaining ether layer 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 2 N-sodium hydroxide aqueous solution
washThe remaining ether layer 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-a58a529d3dcc43d5b190b38142ae8bec
Source dataset: uspto-grants-1982_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04360464

Reaction notes

Loading…