Biphenyl → HCID 22816149, compound

HRID 2287119Notes

Reaction equation

[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li].Cl.Cl[CH2:16][C@@H:17]([N:19]([CH3:21])[CH3:20])[CH3:18].[Cl-].[NH4+]>CCOCC>[CH3:16][C@H:17]([N:19]([CH3:21])[CH3:20])[CH2:18][C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH2:4][CH:3]=[CH:2]1

Participants

Conditions

Temperature: -50 °C

Procedure

28 g. of biphenyl in 300 ml. of absolute ether are added dropwise at about -33° C. while stirring to 360 ml. of dry, condensed ammonia. The mixture is cooled to about -50° C. and 2.5 g. of lithium wire (about 2 cm long pieces, de-greased with cyclohexane) are added over a period of 10 minutes. Then, the mixture is stirred at boiling temperature (about -33° C.) for 2 hours. 9.4 g. of (S)-2-chloro-N,N,1-trimethylethylamine hydrochloride are added portionwise at about -50° C. within about 3 minutes. The mixture is stirred at about -33° C. for 2 hours and subsequently worked-up. After adding ammonium chloride, distilling off of the ammonia, and aqueous working-up and chromatography in analogy to Example 3, there is obtained (S)-α,N,N-trimethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine which is converted in the usual manner into the maleate. After crystallization from ether, the product has a melting point of 87° -90° C.

Workup

customof dry
customcondensed ammonia
stirringThen, the mixture is stirred
customtemperature (about -33° C.)
customfor 2 hours
stirringThe mixture is stirred at about -33° C. for 2 hours
distillationdistilling off of the ammonia

Sources & evidence

ORD record: ord-e6986d0e628b45f28129d752b7094291
Source dataset: uspto-grants-1981_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04269788

Reaction notes

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