N,N-Dimethylethylenediamine → Trans 2-(2-(N,N-dimethylamino)ethyl)aminocarbonyl-4-phenylmethylcarbonylamino-5,7-dichloro-1,2,3,4-tetrahydroquinoline

HRID 484462Notes

Reaction equation

HRID 484462 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C@@H:4]([NH:17][C:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[CH2:5][C@H:6]([C:13]([O:15]C)=O)[NH:7]2.[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][NH2:31]>>[CH3:27][N:28]([CH2:29][CH2:30][NH:31][C:13]([C@H:6]1[CH2:5][C@H:4]([NH:17][C:18]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[NH:7]1)=[O:15])[CH3:32]

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 15168525HCID 15168525, compound

Product 1

HCID 86747050Trans 2-(2-(N,N-dimethylamino)ethyl)aminocarbonyl-4-phenylmethylcarbonylamino-5,7-dichloro-1,2,3,4-tetrahydroquinoline

Procedure

Trans 5,7-dichloro-2-methoxycarbonyl-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline (Example 37a) (0.3 g) was dissolved in N,N-dimethylethylenediamine (30 ml) and allowed to stand at room temperature for 6 h. After this time the reaction mixture was filtered and the solvent was removed under vacuum. The residue was dissolved in ethyl acetate (100 ml) and washed with water (100 ml) then brine (100 ml). The organic solution was dried (MgSO4), filtered and concentrated in vacuo to give a solid which was triturated with diethyl ether and collected by filtration to give the title compound (0.19 g) as a colourless solid, m.p. 158°-159° C.; δ (360 MHz, DMSO) 1.54 (1H, ddd, J=13.0, 12.5 and 4.0 Hz, CHACHBHCCHD), 2.08 (1H, dm, J=13.0 Hz, CHACHBHCCHD), 2.16 (6H, s, N(CH3)2), 2.33 (2H, t, J=6.7 Hz, CH2CH2N(CH3)2, 3.21 (2H, m, CH2CH2N(CH3)2), 3.37 (1H, d, J=14.0 Hz, CHEHFPh), 3.47 (1H, d, J=14.0 Hz, CHEHFPh), 3.74 (1H, dm, J=12.5 Hz, CHACHBHCCHD), 4.99 (1H, m, CHACHBHCCHD), 6.66 (1H, d, J=1.9 Hz, 6-H or 8-H), 6.79 (2H, m, 6-H or 8-H and ArNH), 7.26 (5H, m, ArH), 8.01 (1H, br, s, CONHCH2CH2N(CH3)2), 8.44 (1H, d, J=7.2 Hz, CHDNHCO); m/e 488 (M+); Found C, 58.47; H, 5.84; N, 12.39 C22H26Cl2N4O2 requires C, 58.80; H, 5.83; N, 12.47%.

Workup

  1. filtrationAfter this time the reaction mixture was filtered
  2. customthe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  4. washwashed with water (100 ml)
  5. dry with materialThe organic solution was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a solid which
  9. customwas triturated with diethyl ether
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ab637ca950f14d9baab70ad555b469f9
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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