Water → 3-Chloro-3-(2-pyrazinyl)-1-azabicyclo[2.2.1]heptane

HRID 256875Notes

Reaction equation

S(Cl)([Cl:3])=O.[N:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]1(O)[CH:16]2[CH2:17][N:13]([CH2:14][CH2:15]2)[CH2:12]1.O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:3][C:11]1([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][N:5]=2)[CH:16]2[CH2:17][N:13]([CH2:14][CH2:15]2)[CH2:12]1

Participants

Conditions

Temperature: 60 °C

Procedure

Thionyl chloride (1.5 g, 12.6 mmol) was added to a rapidly stirred solution of 3-(2-pyrazinyl)-1-azabicyclo[ 2.2.1]heptan-3-ol (0.5 g, 2.6 mmol) in dichloromethane (30 ml) at room temperature. The solution was stirred for 1 h, heated at 60° C. for 0.5 h, and then cooled to room temperature, before adding water (20 ml) and basifying with potassium carbonate. Extraction into dichloromethane (3×75 mls), drying (Na2SO4) and chromatography of the residue remaining after removal of solvent through alumina, using ethyl acetate as eluant, gave 3-chloro-3-(2-pyrazinyl)-1-azabicyclo[2.2.1]heptane as a pale yellow oil (0.18 g); m/e 209 (M+ of free base); δ (360 MHz,CDCl3) 0.84-0.92(1H,m,CH of CH2); 1.58-1.67(1H,m,CH of CH2); 2.42-2.48(1H,m,CH of CH2 --N); 2.69-2.72(1H,m,CH of CH2 --N); 2.78-2.86(1H,m,CH of CH2 --N); 3.22-3.24(1H,d, J=4.5 Hz, CH-bridgehead); 3.42-3.49(2H,m,2×CH of CH2 --N); 4.13(1H,dd J=3 and 14 Hz, CH of CH2); 8.48(2H,s,pyrazine-H); 8.91(1H,s,pyrazine-H).

Workup

temperaturecooled to room temperature
extractionExtraction into dichloromethane (3×75 mls)
dry with materialdrying (Na2SO4) and chromatography of the residue
customafter removal of solvent through alumina

Sources & evidence

ORD record: ord-e5b05c2a21d149f2b72a0be03f0bcce7
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05260293

Reaction notes

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