N,N,N',N'-Tetramethylethylenediamine → HCID 14677709, compound

HRID 1165956Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C([Li])CCC.CN(C)CCN(C)C.[CH2:21]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1>CCOCC.O.CCCCCC>[N:5]1[CH:6]=[CH:7][C:2]([C:29]2([OH:30])[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=3[CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:28]2=3)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: -75 °C

Procedure

To a stirred solution of 4-bromopyridine (37.9 g, 0.24 mol) in anhydrous ether (475 mL) at -75° C. under a nitrogen atmosphere was added n-butyllithium (160 mL of a 1.5 M hexane solution, 0.24 mol). Tetramethylethyenediamine (36.2 mL, 0.24 mol) was added and the solution was stirred at -75° C. for 1 hour. A solution of dibenzosuberone (50.l g, 0.24 mol) in anhydrous ether (250 mL) was added dropwise, the reaction mixture was stirred at -75° C. for 40 minutes, warmed to ambient temperature and stirred at that temperature for 1.5 hours. Water (650 mL) was added dropwise. The solid which crystallized was isolated by filtration to give 43.54 g of 10,11-dihydro-5-(4-pyridinyl)-5H-dibenzo[a,d]cyclohepten-5-ol, mp 174-177° C. Recrystallization from ethyl acetate-hexane gave material of mp 183-185° C.

Workup

stirringthe reaction mixture was stirred at -75° C. for 40 minutes
temperaturewarmed to ambient temperature
stirringstirred at that temperature for 1.5 hours
customThe solid which crystallized
customwas isolated by filtration

Sources & evidence

ORD record: ord-5bbf969ff30e49a797f5aa3eea287bf0
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04912222

Reaction notes

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