Dimethylamine → HCID 86753924, compound

HRID 1418697Notes

Reaction equation

HRID 1418697 reaction equation
[CH3:1][NH:2][CH3:3].I[CH2:5][C:6]([O:8][CH:9]([C:12]1[CH:28]=[C:27]2[N:15]([CH2:16][C:17]3[C:18]2=[N:19][C:20]2[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14](=[O:29])[C:13]=1[CH3:30])[CH2:10][CH3:11])=[O:7].C(Cl)[Cl:32]>>[ClH:32].[CH3:30][C:13]1[C:14](=[O:29])[N:15]2[C:27](=[CH:28][C:12]=1[CH:9]([O:8][C:6](=[O:7])[CH2:5][N:2]([CH3:3])[CH3:1])[CH2:10][CH3:11])[C:18]1=[N:19][C:20]3[C:25]([CH:26]=[C:17]1[CH2:16]2)=[CH:24][CH:23]=[CH:22][CH:21]=3

Participants

4

Reactant 3

HCID 674DimethylamineHCID 6344DichloromethaneHCID 86753922HCID 86753922, compound

Product 1

HCID 86753924HCID 86753924, compound

Procedure

A stream of dimethylamine was introduced into a solution containing (±)-7-[1-[(iodoacetyl)oxy]propyl]-8-methylindolizino[1,2-b]quinolin-9(11H)-one (50 mg, 0.11 mmol) in anhydrous CH2Cl2 (15 mL). The resulting solution was allowed to stir for 2 h and then was concentrated under reduced pressure. The residue was partitioned between CH2Cl2 and H2O, and the organic layer was washed several times with H2O and dried over sodium sulfate. Into this solution was bubbled a stream of HCl gas, and the resulting cloudy mixture was stirred for 15 min and then was concentrated in vacuo. The residue was dissolved in H2O and lyophilized to afford the title compound as an orange solid. 1H NMR (DMSO-d6) d 8.68 (s, 1H), 8.15 and 8.12 (two overlapping d, 2H), 7.86 (m, 1H), 7.71 (m, 1H), 7.17 (s, 1H), 5.96 (apparent br t, 1H), 5.26 (s, 2H), 4.41 (s, 2H), 2.84 (br s, 6H), 2.26 (s, 3H), 2.20-1.86 (m, 2H), 0.96 (t, J=7.3 Hz, 3H). CIMS (NH3, m/e, rel. int.) 392 (100) [(M+H)+ ]. Anal. Calcd for C23H25N3O3.2HCl.13/8H2O: C, 55.96; H, 6.18; N, 8.51. Found: C, 56.27; H, 6.03; N, 8.04.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was partitioned between CH2Cl2 and H2O
  3. washthe organic layer was washed several times with H2O
  4. dry with materialdried over sodium sulfate
  5. customInto this solution was bubbled a stream of HCl gas
  6. stirringthe resulting cloudy mixture was stirred for 15 min
  7. concentrationwas concentrated in vacuo
  8. dissolutionThe residue was dissolved in H2O

Sources & evidence

ORD record
ord-8a6194f6026d4b59bab48eaeb9fbc03d
Source dataset
uspto-grants-1999_03
Patent number
US05883255

Reaction notes

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