tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-((6-fluoropyridin-3-yl)methyl)piperazine-1-carboxylate

HRID 1811806Notes

Reaction equation

HRID 1811806 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[N:20][CH:21]=1>CN(C)C=O>[F:22][C:19]1[N:20]=[CH:21][C:16]([CH2:15][N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 220506385-(Bromomethyl)-2-fluoropyridine

Product 1

HCID 59548414Tert-butyl 4-((6-fluoropyridin-3-yl)methyl)piperazine-1-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl piperazine-1-carboxylate (Aldrich, St. Louis, Mo., 17.77 g, 95 mmol) was added to a stirred solution of 5-(bromomethyl)-2-fluoropyridine (15.11 g, 80 mmol) in N,N-dimethylformamide (120 mL) at 0° C. and the suspension was stirred at room temperature overnight. The resulting thick reaction mixture was quenched with cold water (50 mL), the resulting suspension was stirred for 30 min, and the resulting solid was collected and washed with additional cold water (50 mL). The off-white precipitate was dried under vacuum to give the title compound tert-butyl 4-((6-fluoropyridin-3-yl)methyl)piperazine-1-carboxylate (19.7494 g, 66.9 mmol, 84% yield) as a white solid. LCMS (API-ES) m/z 296 (M+H)+; 1H NMR (400 MHz, d6-DMSO) δ 8.13 (s, 1H) 7.90 (td, J=8.02, 1.37 Hz, 1H) 7.15 (dd, J=8.31, 2.05 Hz, 1H) 3.51 (s, 2H) 3.30 (br. s., 4H) 2.10-2.40 (m, 4H) 1.39 (s, 9H).

Workup

  1. customThe resulting thick reaction mixture was quenched with cold water (50 mL)
  2. stirringthe resulting suspension was stirred for 30 min
  3. customthe resulting solid was collected
  4. washwashed with additional cold water (50 mL)
  5. customThe off-white precipitate was dried under vacuum

Sources & evidence

ORD record
ord-c03226f8626c4fb4a7dd5c4e3ef50d9c
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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