Decalin → 5-(4-(2-hydroxyethyl)phenyl)-5H-dibenz[b,f]azepine

HRID 2227127Notes

Reaction equation

[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.I[C:17]1[CH:25]=[CH:24][C:20]([CH2:21][CH2:22][OH:23])=[CH:19][CH:18]=1.[OH-].[K+].C1C2C(CCCC2)CCC1>[Cu].C(Cl)(Cl)Cl>[OH:23][CH2:22][CH2:21][C:20]1[CH:24]=[CH:25][C:17]([N:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9]=[CH:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 8.7 g (45 mmol) of 5H-dibenz[b,f]azepine, 12.4 g (50 mmol) of p-iodophenethyl alcohol, 2.8 g (50 mmol) of potassium hydroxide, 4.8 g (75 mmol) of copper powder, and 20 ml of decalin was heated at an external temperature of 200° C. while stirring in a nitrogen stream for 40 hours. The reaction mixture was cooled nearly to room temperature, chloroform was added thereto, followed by filtration using Celite to remove any insoluble matter. The filtrate was concentrated. To remove decalin, n-hexane was added to the residue, followed by filtration. The filter cake was reprecipitated in methanol, and the resulting crude product was purified by silica gel column chromatography to give 4.2 g (30%) of 5-(4-(2-hydroxyethyl)phenyl)-5H-dibenz[b,f]azepine.

Workup

temperatureThe reaction mixture was cooled nearly to room temperature
filtrationfollowed by filtration
customto remove any insoluble matter
concentrationThe filtrate was concentrated
customTo remove decalin, n-hexane
additionwas added to the residue
filtrationfollowed by filtration
customThe filter cake was reprecipitated in methanol
customthe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-43be315c48004880a214528c539fd109
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06413657B1

Reaction notes

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