Sulfuric Acid → 1-[1-(4-Aminophenyl)-2-dimethylaminoethyl]cyclohexanol

HRID 485141Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]([N:18]([CH3:20])[CH3:19])=O)[C:9]2([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O>O1CCCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]2([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:16][N:18]([CH3:20])[CH3:19])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5.0 g (0.018 mole) of the above amide was dissolved in 300 ml of dry tetrahydrofuran and added dropwise to a mixture of 1.1 g of lithium aluminum hydride and 8.0 ml of concentrated sulfuric acid in 200 ml of tetrahydrofuran at 0° C. The mixture was stirred at 0° C. for five hours, then the excess reagent was destroyed by the dropwise addition of 4 ml of 50:50 THF-water, then 4 ml of 15% aqueous sodium hydroxide and finally 4 ml of water. The mixture was filtered and the precipitate washed several times with THF. The combined filtrates were evaporated and the residue recrystallized from isopropanol to give 3.8 g of the title compound as the free base. Treatment with excess oxalic acid in ethyl acetate gave the dioxalate, m.p. 105° C.(d).

Workup

customthe excess reagent was destroyed by the dropwise addition of 4 ml of 50:50 THF-water
filtrationThe mixture was filtered
washthe precipitate washed several times with THF
customThe combined filtrates were evaporated
customthe residue recrystallized from isopropanol

Sources & evidence

ORD record: ord-845c09403a8b4b9aa950ad876b7627de
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04535186

Reaction notes

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