Ammonium Hydroxide → Phenol, 3-(1-ethyl-1,2,5,6-tetrahydro-3-pyridinyl)-

HRID 851142Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:10][N:11]([CH2:15][CH3:16])[CH2:12][CH2:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.Cl.[NH+]1C=CC=CC=1.[OH-].[NH4+]>O>[CH2:15]([N:11]1[CH2:12][CH2:13][CH:14]=[C:9]([C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)[CH2:10]1)[CH3:16]

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 5.2 g of the product of Step A and 10.4 g of pyridinium hydrochloride was heated at 200° C. for 21/2 hours and the mixture was cooled and diluted with water. Ammonium hydroxide was added to the mixture which was then extracted with methylene chloride. The organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 6-3-1 cyclohexane-chloroform-triethylamine mixture to obtain 3.95 g of 3-(1-ethyl-1,2,5,6-tetrahydropyridin-3-yl)-phenol. 3.85 g of the latter were dissolved in 40 ml of isopropanol and 2.4 g of oxalic acid were added thereto. The mixture was cooled and filtered and the product was washed with isopropanol and dried to obtain 3.57 g of 3-(1-ethyl-1,2,5,6-tetrahydropyridin-3-yl)-phenol oxalate melting at 240° C.

Workup

temperaturethe mixture was cooled
extractionwas then extracted with methylene chloride
washThe organic phase was washed with water
customdried
customevaporated to dryness under reduced pressure
customThe residue was chromatographed over silica gel
washwas eluted with a 6-3-1 cyclohexane-chloroform-triethylamine mixture

Sources & evidence

ORD record: ord-3d63e03a188c48f89ad514959e2eff0a
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04382942

Reaction notes

Loading…