Dimethylformamide → 78484-03-4

HRID 1979775Notes

Reaction equation

HRID 1979775 reaction equation
[OH:1][CH:2]([CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:15])[NH:10]2.C[I:30].[CH3:31]N(C)C=O>CC(C)=O>[I-:30].[C:23]1([CH:20]2[CH2:19][CH2:18][N+:17]([CH2:16][CH:2]([OH:1])[CH2:3][O:4][C:5]3[CH:14]=[CH:13][CH:12]=[C:11]4[C:6]=3[CH2:7][CH2:8][C:9](=[O:15])[NH:10]4)([CH3:31])[CH2:22][CH2:21]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 12783759HCID 12783759, compound

Product 1

HCID 306101478484-03-4

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.0 Grams of 5-[2-hydroxy-3-(4-phenyl-1-piperidyl)propoxy]-3,4-dihydrocarbostyril and 3 g of methyl iodide were mixed with 30 ml of dimethylformamide and the mixture was stirred at 50°-60° C. for 5 hours. The reaction mixture was concentrated under a reduced pressure and to the residue thus obtained was added 50 ml of acetone and stirred. The precipitates thus formed were collected by filtration and washed with acetone, then recrystallized from methanol-ethanol to obtain 1.7 g of 4-phenyl-1-[2-hydroxy-3-(2-oxo-1,2,3,4-tetrahydroquinolin-5-yloxy)propyl]-1-methylpiperidiniumiodide as in the form of colorless powdery substance. Melting point: 242°-243° C.

Workup

  1. concentrationThe reaction mixture was concentrated under a reduced pressure and to the residue
  2. customthus obtained
  3. stirringstirred
  4. customThe precipitates thus
  5. customformed
  6. filtrationwere collected by filtration
  7. washwashed with acetone
  8. customrecrystallized from methanol-ethanol

Sources & evidence

ORD record
ord-5efdf3e0154d4c9eb72d29f9c0f4f1e9
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

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