Dichloromethane → HCID 21699495, compound

HRID 1597268Notes

Reaction equation

HRID 1597268 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH2:13]([N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(Cl)[Cl:28]>C1COCC1.CCCCCC>[ClH:28].[CH2:13]([N:20]1[CH2:25][CH2:24][C:23]([OH:26])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 79732-BromopyridineHCID 192201-Benzyl-4-piperidoneHCID 178418339Butyllithium

Product 1

HCID 21699495HCID 21699495, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

25 g of 2-bromopyridine are dissolved in 100 ml of THF at −70° C., under nitrogen, and a 1.6M solution of n-butyllithium in hexane is added dropwise followed by a solution of 30 g of 1-benzyl-piperid-4-one in 25 ml of THF. The temperature is allowed to rise to RT, and, after one hour, the solvents are partially evaporated, the residue is poured over a saturated solution of NH4Cl, extracted with ether, washed with water, dried over MgSO4 and evaporated. An oil is obtained which is dissolved in 200 ml of DCM and gaseous HCl is bubbled so as to form the hydrochloride. The expected product (21 g) crystallizes from a methanol/ether mixture, m.p.=185° C.

Workup

  1. customto rise to RT
  2. customthe solvents are partially evaporated
  3. additionthe residue is poured over a saturated solution of NH4Cl
  4. extractionextracted with ether
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customAn oil is obtained which
  9. customgaseous HCl is bubbled so as

Sources & evidence

ORD record
ord-14193cc42e9b45a293461ae759e6d629
Source dataset
uspto-grants-2001_09
Patent number
US06294537B1

Reaction notes

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