Dichloromethane → HCID 131724535, compound

HRID 1836571Notes

Reaction equation

HRID 1836571 reaction equation
O=[C:2]1[N:13]2[C:14]3[C:9]([CH2:10][CH2:11][CH2:12]2)=[CH:8][CH:7]=[CH:6][C:5]=3[CH:4]=[C:3]1[C:15](OCC)=O.CO[CH2:22][N:23](CC1C=CC=CC=1)C[Si](C)(C)C.FC(F)(F)C(O)=O.C(Cl)[Cl:44]>>[ClH:44].[ClH:44].[CH:6]1[CH:7]=[CH:8][C:9]2[CH2:10][CH2:11][CH2:12][N:13]3[C:14]=2[C:5]=1[C@@H:4]1[CH2:22][NH:23][CH2:15][C@@H:3]1[CH2:2]3

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 23498526Ethyl 2,3-dihydro-5-oxo-1H,5H-benzo[ij]quinolizine-6-carboxylate

Product 1

HCID 131724535HCID 131724535, compoundYield 96%

Conditions

Temperature
40 °C

Procedure

To a solution of ethyl 5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylate (25.0 g, 97 mmol) in 400 mL of methylene chloride was added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (46.1 g, 194 mmol) and trifluoroacetic acid (2.22 g, 19 mmol). The reaction mixture was stirred at 40° C. for 24 h. The reaction mixture was allowed to cool and was washed with sat'd aq. NaHCO3 and brine, dried (K2CO3) and concentrated in vacuo. The residue was purified by recrystallization from 4:1 hexane/ethyl acetate to afford 36.6 g (96%) of the title compound of Part B as an off white solid. 1H NMR (CDCl3) δ: 7.37-7.20 (m, 5H), 7.05-7.00 (m, 1H), 6.97-6.88 (m, 2H), 4.28-4.19 (m, 1H), 4.12-4.01 (m, 2H), 3.80-3.68 (m, 4H), 3.57 (ABq, 2H, JAB=10.2 Hz), 3.17 (app t, 1H, J=8.8 Hz), 2.85-2.77 (m, 2H), 2.49 (app t, 1H, J=9.5 Hz), 2.05-1.95 (m, 2H), 1.09 (t, 3H, J=7.0 Hz).

Workup

  1. temperatureto cool
  2. washwas washed with sat'd aq. NaHCO3 and brine
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by recrystallization from 4:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-64ea401fa98947728836247a96c76b92
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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