Dimethylformamide → 2-(3,4-Dichlorophenyl)-1-{4-[(2-Piperidyl)Ethoxy]Benzyl}-1,2,3,4-Tetrahydroisoquinolin-6-Ol

HRID 2304672Notes

Reaction equation

HRID 2304672 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19]CC4C=CC=CC=4)[CH:15]=3)[CH:10]2[CH2:27][C:28]2[CH:33]=[CH:32][C:31](O)=[CH:30][CH:29]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:35](=[O:38])([O-])[O-].[K+].[K+].Cl.ClCC[N:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1.[CH3:51]N(C=O)C>>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=3)[CH:10]2[CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:38][CH2:35][CH2:51][CH:50]3[CH2:49][CH2:48][CH2:47][CH2:46][NH:45]3)=[CH:30][CH:29]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 234407442-(3,4-Dichlorophenyl)-1-(4-hydroxybenzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 693128582-(3,4-Dichlorophenyl)-1-{4-[(2-Piperidyl)Ethoxy]Benzyl}-1,2,3,4-Tetrahydroisoquinolin-6-OlYield 70%

Procedure

To a solution of 2-(3,4-dichlorophenyl)-1-(4-hydroxybenzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline (0.5 g, 0.001 mol) in DMF (3 ml) was added potassium carbonate (0.2 g, 0.0015 mol). The reaction was allowed to stir for twenty minutes. To the flask was added 1-(2-chloroethyl)piperidine monohyrdochloride (0.22 g, 0.0012 mol). The reaction was allowed to stir at 80° C. overnight. Solvent was removed. The reaction was diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over MgSO4, filtered and concentrated to yield the title compound (0.42 g, 70% yield): ES-MS (m/z) 601 [M+H]+.

Workup

  1. stirringto stir at 80° C. overnight
  2. customSolvent was removed
  3. additionThe reaction was diluted with ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-725a2219025a4d7a8208aa286132623b
Source dataset
uspto-grants-2002_08
Patent number
US06436923B1

Reaction notes

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