Pyridine → HCID 86735673, compound

HRID 371748Notes

Reaction equation

HRID 371748 reaction equation
[C:1]12([CH2:10][NH2:11])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.N1C=CC=CC=1.[Br:18][CH2:19][C:20](Br)=[O:21]>CCOCC>[Br:18][CH2:19][C:20]([NH:11][CH2:10][C:1]12[C:7]([CH3:8])([CH3:9])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2)=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 20356306HCID 20356306, compound

Product 1

HCID 86735673HCID 86735673, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

10-Bornanamine (0.5 g) in dry ether (30 ml) containing pyridine (C.45 ml) was treated at -80° with a solution of bromoacetyl bromide (0.3 ml) in ether (5 ml) over one minute with stirring. The mixture was allowed to warm to room temperature and after a further 30 min. it was partitioned between ether and water. The organic layer was washed with 2N-hydrochloric acid solution and then water. It was dried (MgSO4) and evaporated. The residue (0.73 g.) was purified by preparative layer chromatography and by crystallisation from petroleum ether (bp. 60°-80°) to give the title compound (0.48 g) mp. 89°, (Found: C, 52.4; H, 7.3; Br, 28.9; N, 5.0; C12H20BrNO requires C, 52.55; H, 7.35; Br, 29.1; N,5.1%).

Workup

  1. customwas partitioned between ether and water
  2. washThe organic layer was washed with 2N-hydrochloric acid solution
  3. dry with materialIt was dried (MgSO4)
  4. customevaporated
  5. customThe residue (0.73 g.) was purified by preparative layer chromatography and by crystallisation from petroleum ether (bp. 60°-80°)

Sources & evidence

ORD record
ord-990b80b6787a460ba77c0ccfcf2271c7
Source dataset
uspto-grants-1978_05
Patent number
US04087551

Reaction notes

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