Triethylamine → HCID 21793852, compound

HRID 1729991Notes

Reaction equation

HRID 1729991 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:18][CH3:19])=[CH:5][C:6]2[C:15]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[C:9](=[O:16])[NH:8][C:7]=2[CH:17]=1.Cl.Cl[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(N(CC)CC)C>C(O)C>[CH3:1][O:2][C:3]1[C:4]([O:18][CH3:19])=[CH:5][C:6]2[C:15]3[CH2:14][CH2:13][N:12]([CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[CH2:11][C:10]=3[C:9](=[O:16])[NH:8][C:7]=2[CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 21793850HCID 21793850, compound

Product 1

HCID 21793852HCID 21793852, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.2 g (0.02 m) of 1,2,3,4-tetrahydro-8,9-dimethoxybenzo[c][2,7]naphthyridin-5(6H)-one, 4.05 g (0.022m) of N-(2-chloroethyl)piperidine HCl and 4.45 g (0.044 m) of triethylamine in 125 cc of ethyl alcohol was refluxed for 18 hr. After evaporation, the residue was dissolved in 100 ml of water, made strongly basic with conc NH4OH solution and extracted with three 50 ml portions of chloroform. The chloroform extract was dried (Na2SO4) and evaporated in vacuo. The residue was crystallized from acetonitrile affording 3.3 g (44% of crude material. Recrystallization from 2-propanol afforded analytical material, mp 185°-188° C.

Workup

  1. customAfter evaporation
  2. dissolutionthe residue was dissolved in 100 ml of water
  3. extractionextracted with three 50 ml portions of chloroform
  4. extractionThe chloroform extract
  5. dry with materialwas dried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was crystallized from acetonitrile affording 3.3 g (44% of crude material
  8. customRecrystallization from 2-propanol afforded analytical material, mp 185°-188° C.

Sources & evidence

ORD record
ord-fd554b3c7dd645fd92ed41f740a4a24d
Source dataset
uspto-grants-1976_11
Patent number
US03991064

Reaction notes

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