Dichloromethane → HCID 89677027, compound

HRID 2278269Notes

Reaction equation

HRID 2278269 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]=O)[CH:3]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.ClCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)[CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 147614724-Bromopyridine-2-carbaldehyde

Product 1

HCID 89677027HCID 89677027, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round-bottom flask was charged with 4-bromopyridine-2-carbaldehyde (1.60 g, 8.60 mmol, 1.07 equiv), tert-butyl piperazine-1-carboxylate (1.50 g, 8.05 mmol, 1.00 equiv), and dichloromethane (30 mL). The mixture was stirred for 30 min at room temperature. Sodium triacetoxyborohydride (5.10 g, 24.1 mmol, 3.00 equiv) was added. The resulting solution was stirred for overnight at room temperature and then diluted with water (30 mL). The resulting mixture was extracted with dichloromethane (2×20 mL) and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (45/55) to provide 2.70 g (94% yield) of tert-butyl 4-[(4-bromopyridin-2-yl)methyl]piperazine-1-carboxylate as a yellow solid. LCMS (ESI, m/z): 356 [M+H]+.

Workup

  1. stirringThe resulting solution was stirred for overnight at room temperature
  2. extractionThe resulting mixture was extracted with dichloromethane (2×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (45/55)

Sources & evidence

ORD record
ord-cda0aa58eff741108abee26999c817b8
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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