Potassium Bromide → 5-(2-Bromo-ethyl)-5, 6-dihydro-phenanthridine

HRID 550856

Reaction equation

HRID 550856 reaction equation
CN(C=O)C.CCO[CH2:9][CH3:10].[K+].[Br-:12].[Br-].BrCC[C:17]1[C:30]2[C:21](=[NH+:22][CH:23]=[C:24]3[C:29]=2[CH:28]=[CH:27][CH:26]=[CH:25]3)[CH:20]=[CH:19][CH:18]=1>C(OCC)(=O)C>[Br:12][CH2:24][CH2:23][N:22]1[CH2:9][C:10]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:30]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]1=2

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 19966313DMF etherHCID 671881532-Bromo-ethyl-phenanthridinium bromide

Product 1

HCID 111969725-(2-Bromo-ethyl)-5, 6-dihydro-phenanthridineYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

During the preparation of 6a, the mother liquor from the DMF/ether (25:75) solution was kept and washed thoroughly 4 times with 40 ml of water. The organic layer was then washed with brine and dried over MgSO4. The solvent was evaporated down to a dark residue. Column chromatography (Silica, DCM as elutant) afforded 5 (140 mg; 0.485 mmol) as a beige powder in a 50% yield. Rf=0.75 in 100% ethyl acetate; mp: 99-100° C.; 1H NMR (CDCl3, 400 MHz): δ 7.64 (d, 1H, J=7.60 Hz), 7.60 (d, 1H, J=7.60 Hz), 7.22 (t, 1H, J=7.60 Hz), 7.13 (t, 2H, J=7.60 Hz), 7.01 (d, 1H, J=7.60 Hz), 6.77 (t, 1H, J=7.60 Hz), 6.62 (d, 1H, J=7.60 Hz), 4.27 (s, 2H), 3.64 (t, 2H, J=7.80 Hz), 3.44 (t, 2H, J=7.80 Hz); 13C NMR (CDCl3, 100 MHz): δ 145.02 (C), 132.71 (C), 132.19 (C), 129.68 (CH), 128.55 (CH), 128.22 (CH), 125.96 (CH), 124.44 (CH), 124.22 (C), 123.59 (CH), 119.19 (CH), 112.51 (CH), 53.38 (CH2), 53.26 (CH2), 27.78 (CH2); IR (KBr, cm−1): 3429 (s), 2924 (w), 1716 (w), 1628 (s), 1601 (s), 1525 (w), 1493 (s), 1442 (s), 1340 (m), 1290 (m), 1269 (s), 1196 (s), 1022 (m), 758 (s), 725 (m), 615 (m) MS (FAB): 289 (M+H) (100), 222.1 (7), 194.1 (35), 180.1 (22), 166.1 (6), 152.1 (4), 107.2 (2), 85.7 (1), 58.1 (7); Anal. Calcd for C15H14NBr: C, 62.51; H, 4.89; N, 4.86. Found: C, 62.30; H, 4.96; N, 4.75.

Workup

  1. washwashed thoroughly 4 times with 40 ml of water
  2. washThe organic layer was then washed with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated down to a dark residue
  5. customColumn chromatography (Silica, DCM as elutant) afforded 5 (140 mg; 0.485 mmol) as a beige powder in a 50% yield

Sources & evidence

ORD record
ord-9aa5a46564204afabee6e8f062b4d207
Source dataset
uspto-grants-2011_05
Patent number
US07947703B2

Linked notes

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