N,N,N',N'-Tetramethylethylenediamine → HCID 22759855, compound

HRID 1703816Notes

Reaction equation

HRID 1703816 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH:9]2[CH2:14][CH:13]3[CH2:15][CH2:16][N:10]2[CH2:11][CH2:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CN(CCN(C)C)C.[CH2:36](Br)[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>CCCCCC.C1CCCCC1>[C:17]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:8][CH:9]2[CH2:14][CH:13]3[CH2:15][CH2:16][N:10]2[CH2:11][CH2:12]3)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 81011-BromohexaneHCID 20339673HCID 20339673, compoundHCID 178418339Butyllithium

Product 1

HCID 22759855HCID 22759855, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8078CyclohexaneSolvent

Procedure

Following the procedure which is described in Example 4, 2.91 parts of 2-(2,2-diphenylethyl)-1-azabicyclo[2.2.2]octane in 40 parts by volume of cyclohexane, 5.1 parts by volume of a 2.17 M solution of butyl lithium in hexane are reacted with 1.5 parts of TMEDA and 1.81 parts of n-hexyl bromide to provide 2-(2,2-diphenyloctyl)-1-azabicyclo[2.2.2]octane. This compound is then treated with 0.730 parts of maleic acid to give 2-(2,2-diphenyloctyl)-1-azabicyclo[2.2.2]octane maleate, melting at about 180°-181° C. This compound is represented by the following structural formula ##STR10##

Sources & evidence

ORD record
ord-a35a5fae473a4ce18fdd81e67eabc9c3
Source dataset
uspto-grants-1978_11
Patent number
US04125531

Reaction notes

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