Dimethylformamide → HCID 54197798, compound

HRID 1180139Notes

Reaction equation

HRID 1180139 reaction equation
O[C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.Cl.ClCC[N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.[C:37](=[O:40])([O-])[O-].[K+].[K+].[Cl-].[NH4+].[CH3:45]N(C)C=O>O>[CH3:18][O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[CH:7]([CH2:6][C:5]1[CH:25]=[CH:26][C:2]([O:40][CH2:37][CH2:45][CH:36]3[CH2:35][CH2:34][CH2:33][CH2:32][NH:31]3)=[CH:3][CH:4]=1)[N:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:9][CH2:10]2

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 12992436HCID 12992436, compound

Product 1

HCID 54197798HCID 54197798, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-(4-hydroxybenzyl)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroisoquinoline (0.30 g, 0.87 mmol), 2-chloroethylpiperidine hydrochloride (0.32 g, 1.74 mmol) and potassium carbonate (0.24 g, 1.74 mmol) in dimethyl formamide (15 mL) was heated to 80° C. After 6 hours, the mixture was cooled to RT, poured into water (30 mL), and neutralized using a saturated solution of ammonium chloride. The product was extracted with ethyl acetate (2×75 mL), dried over MgSO4, filtered and concentrated. The residue was then chromatographed (SiO2, 10:1 ethyl acetate/ethanol) to provide the title compound (0.20 g, 47% yield): ES-MS (m/z) 457 [M+H]+.

Workup

  1. extractionThe product was extracted with ethyl acetate (2×75 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was then chromatographed (SiO2, 10:1 ethyl acetate/ethanol)

Sources & evidence

ORD record
ord-67562641079146ee82bb086437202bc0
Source dataset
uspto-grants-2007_10
Patent number
US07279489B2

Reaction notes

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