Ammonium Hydroxide → 3-[1-(2-Phenylethyl)-1,2,5,6-tetrahydropyridin-3-yl]phenol

HRID 851140Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:10][N:11]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[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)[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 6 g of the product of Step A and 12 g of pyridinium hydrochloride was heated at 200° C. with stirring 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. The residue was chromatographed over silica gel and was eluted with an 8-2 chloroform-acetone mixture to obtain 4.9 g of 3-(1-phenethyl-1,2,5,6-tetrahydropyridin-3-yl)-phenol melting at 155° C.

Workup

temperaturethe mixture was cooled
extractionwas then extracted with methylene chloride
washThe organic phase was washed with water
customdried
customevaporated to dryness
customThe residue was chromatographed over silica gel
washwas eluted with an 8-2 chloroform-acetone mixture

Sources & evidence

ORD record: ord-7b58f8ff1c0e41b0a9593bb9cc60ef3f
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04382942

Reaction notes

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