Sodium Carbonate → 1-Piperazinebutanenitrile, 4-(2-pyrimidinyl)-

HRID 256573Notes

Reaction equation

HRID 256573 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]2CCC3(CCCC3)CC2)[CH2:9][CH2:8]1.N1C=CC=NC=1N1CCNCC1.ClCCCC#N.C([O-])([O-])=O.[Na+].[Na+]>C(O)CCC>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][C:16]#[N:17])[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 123364-ChlorobutyronitrileHCID 887471-(2-Pyrimidinyl)piperazineHCID 23358116HCID 23358116, compound

Product 1

HCID 3986541-Piperazinebutanenitrile, 4-(2-pyrimidinyl)-

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

For example, 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4,5]decane is prepared by the condensation of 1-(2-pyrimidinyl)piperazine with 3-chloro-1-cyanopropane by means of Na2CO3 in n-butanol gives 4-(2-pyrimidinyl)-1-(3-cyanopropyl)piperazine which is reduced with LiAlH4 or with H2 and Raney nickel (RaNi) yielding 4-(2-pyrimidinyl)-1-(4-aminobutyl)piperazine, which is finally condensed with 8-oxaspiro [4,5]decane-7,9-dione (3,3-tetramethyleneglutaric anhydride) in pyridine.

Sources & evidence

ORD record
ord-d07b26309ae7471bbbb07c8870ac0826
Source dataset
uspto-grants-1993_11
Patent number
US05258379

Reaction notes

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