Hydrochloric Acid → HCID 9861328, compound
Reaction equation
[Si](C1C(C#C)=C(OC2C=CC=C([Si](C)(C)C)C=2C#C)C=CC=1)(C)(C)C.C([O-])([O-])=O.[K+].[K+].[I-].[K+].[C:34]([C:36]1[CH:53]=[CH:52][C:39]([O:40][CH2:41][CH2:42][CH2:43][N:44]2[CH2:49][CH:48]3[CH2:50][CH2:51][CH:45]2[CH2:46][CH2:47]3)=[CH:38][CH:37]=1)#[CH:35].[ClH:54]>C(OCC)C>[ClH:54].[C:34]([C:36]1[CH:37]=[CH:38][C:39]([O:40][CH2:41][CH2:42][CH2:43][N:44]2[CH2:49][CH:48]3[CH2:47][CH2:46][CH:45]2[CH2:51][CH2:50]3)=[CH:52][CH:53]=1)#[CH:35]Participants
Procedure
In the b) route of scheme 2,2-azabicyclo[2.2.2]octane hydrochloride (isoquinuclidine hydrochloride) (8) is reacted with TMS-ethynyl-phenyl ether derivative (3) in the presence of K2CO3 and potassium iodide (KI). The resulting 2-[3-(4-ethynylphenoxy)propane-1-yl]-2-azabicyclo[2.2.2]octane (9) is treated with ethyl ether solution in saturated hydrochloride gas (HCl gas in ether) to obtain 2-[3-(4-ethynylphenoxy)propane-1-yl]-2-azabicyclo[2.2.2]octane hydrochloride (compound 10). Further, this compound 10 is treated with n-BuLi, then it is reacted with ethyl chloroformate in tetrahydrofuran (THF) to give an ethyl 4-[3-(2-azabicyclo[2.2.2]octan-2-yl)propoxy]phenylpropiolate (11), then it is treated by the same method as mentioned above to provide an ethyl 4-[3-(2-azabicyclo[2.2.2]octan-2-yl)propoxy]phenylpropiolate hydrochloride (compound 12). In case of both R1 and R2 are hydrogen and m is 0 or 2 in the compounds of general formula (1), compound 13 (m=0) and compound 14 (m=2), it is prepared by the same method of scheme 1 and a) route of scheme 2 using either a 1,2-dibromoethane or a 1,4-dibromobutane in the place of a 1-bromo-3-chloropropane. ##STR4##
Sources & evidence
- ORD record
- ord-165de4b0b59a491a9a546e97779b7f6f
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124460
Reaction notes
Loading…