3-Bromopyridine → HCID 15045442, compound

HRID 1110361Notes

Reaction equation

HRID 1110361 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]1[CH2:24][CH2:23][N:22]([CH:25]2[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26]2)[CH2:21][CH2:20]1>C(OCC)C.O1CCCC1>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:28]2([OH:31])[CH2:29][CH2:30][CH:25]([N:22]3[CH2:23][CH2:24][N:19]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=4)[CH2:20][CH2:21]3)[CH2:26][CH2:27]2)[CH:3]=1

Participants

6

Reactant 3

HCID 122863-BromopyridineHCID 11807407HCID 11807407, compoundHCID 178418339Butyllithium

Product 1

HCID 15045442HCID 15045442, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.74 g (30 mmol) of 3-bromopyridine in 100 ml of diethyl ether is cooled to --78° C. under a nitrogen atmosphere. n-Butyllithium (18.75 ml, 30 mmol) is added dropwise. The resulting suspension is stirred for 30 minutes. To this solution is added a solution of 5.19 g of 4-[4-(2-pyridinyl)-1-piperazinyl]cyclohexanone in 175 ml of tetrahydrofuran dropwise. The cold bath is removed and the mixture is allowed to warm to room temperature and quenched with 50 ml of saturated ammonium chloride solution. The tetrahydrofuran is evaporated under vacuum and the residue is partitioned into water/dichloromethane. The organic phase is separated and dried over magnesium sulfate and evaporated in vacuo to give the title compound as a mixture of cis and trans isomers.

Workup

  1. customThe cold bath is removed
  2. customquenched with 50 ml of saturated ammonium chloride solution
  3. customThe tetrahydrofuran is evaporated under vacuum
  4. customthe residue is partitioned into water/dichloromethane
  5. customThe organic phase is separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-d212eec3fe5f435fa37a52fed8a5380d
Source dataset
uspto-grants-1990_12
Patent number
US04975445

Reaction notes

Loading…