Sodium Hydroxide → HCID 67945615, compound

HRID 1650966Notes

Reaction equation

[CH:1]([NH:3][CH:4]([C:11]1([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:14][CH2:13][CH2:12]1)[CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH3:10])=O.[H-].COCCO[Al+]OCCOC.[Na+].[H-].COCCO[AlH2-]OCCOC.[Na+].[OH-].[Na+].[C:50]([OH:57])(=[O:56])/[CH:51]=[CH:52]\[C:53]([OH:55])=[O:54]>C1(C)C=CC=CC=1.O>[C:50]([OH:57])(=[O:56])/[CH:51]=[CH:52]\[C:53]([OH:55])=[O:54].[CH3:1][NH:3][CH:4]([C:11]1([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH2:14][CH2:13][CH2:12]1)[CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH3:10]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of N-formyl-1-[1-(4-chlorophenyl)cyclobutyl]-4-ethoxybutylamine (1.6 g) in dry toluene (40 ml) was added dropwise to a stirred 70% solution of sodium bis-(2-methoxyethoxy)aluminium hydride in toluene sold under the trade name Red-Al (6 ml) in dry toluene (15 ml) at ambient temperature, under nitrogen. The mixture was stirred at 50° C. for 3 hours then cooled and water (20 ml) and then 5N sodium hydroxide solution (15 ml) were added. The mixture was extracted with ether and the extracts dried and evaporated to give an oil which was treated with an ethereal solution of maleic acid to give a salt which was recrystallised from propan-2-ol to give N-methyl-1-[1-(4-chlorophenyl)cyclobutyl]-4-ethoxybutylamine maleate (m.p. 102°-103° C.).

Workup

temperaturethen cooled
extractionThe mixture was extracted with ether
customthe extracts dried
customevaporated
customto give an oil which
customto give a salt which
customwas recrystallised from propan-2-ol

Sources & evidence

ORD record: ord-4239bd397272415d8755bebad13176ce
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04925879

Reaction notes

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