Water → 5-Chloro-1',2',3',6'-tetrahydro-2,4'-bipyridine

HRID 2043102Notes

Reaction equation

HRID 2043102 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1.C(OC([N:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1)=O)(C)(C)C.O>C(OCC)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:24]2[CH2:25][CH2:26][NH:21][CH2:22][CH:23]=2)=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 8170982-Bromo-5-chloropyridineHCID 178418339Butyllithium

Product 1

HCID 211055245-Chloro-1',2',3',6'-tetrahydro-2,4'-bipyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Butyllithium (15% in hexane; 7.6 ml) was added dropwise to a solution of 2-bromo-5-chloropyridine (2.0 g) in diethyl ether (50 ml) at −78° C. and, after one hour, a solution of N-tert-butoxycarbonyl-4-piperidinone (2.1 g) in diethyl ether (10 ml) was added dropwise. After 30 minutes, water was cautiously added, and the mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was treated with thionyl chloride (3 g) for 24 hours, and the concentrated reaction solution was purified by preparative HPLC. The product with the molecular weight of 194.67 (C10H11ClN2); MS (ESI): 195 (M+H+) was obtained in this way.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe residue was treated with thionyl chloride (3 g) for 24 hours
  6. customthe concentrated reaction solution
  7. customwas purified by preparative HPLC
  8. customMS (ESI): 195 (M+H+) was obtained in this way

Sources & evidence

ORD record
ord-7a501a4db8d74e939a09f6a3e9b5e4d3
Source dataset
uspto-grants-2013_11
Patent number
US08586609B2

Reaction notes

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