Dimethylformamide → 1-[4-(4-{[1-benzhydrylazetidin-3-yl]methoxy}phenyl)tetrahydro-2H-pyran-4-yl]-N,N-dimethylmethanamine

HRID 272995Notes

Reaction equation

HRID 272995 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)[CH3:3].Cl.[CH:19]([N:32]1[CH2:35][CH:34]([CH2:36]Cl)[CH2:33]1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH:19]([N:32]1[CH2:35][CH:34]([CH2:36][O:17][C:14]2[CH:15]=[CH:16][C:11]([C:5]3([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:6][CH2:7][O:8][CH2:9][CH2:10]3)=[CH:12][CH:13]=2)[CH2:33]1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenolHCID 68576193HCID 68576193, compound

Product 1

HCID 685784331-[4-(4-{[1-benzhydrylazetidin-3-yl]methoxy}phenyl)tetrahydro-2H-pyran-4-yl]-N,N-dimethylmethanamineYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (1.15 g, 5.65 mmol), 1-benzhydryl-3-chloromethyl-azetidine hydrochloride (1.58 g, 5.13 mmol), N,N-dimethylformamide (32 ml) and potassium carbonate (2.84 g, 20.52 mmol) were reacted together according to general procedure B. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with 2M sodium hydroxide (3×50 ml), brine (3×50 ml), dried over magnesium sulphate, filtered and concentrated in vacuo to provide 1-[4-(4-{[1-benzhydrylazetidin-3-yl]methoxy}phenyl)tetrahydro-2H-pyran-4-yl]-N,N-dimethylmethanamine (1.82 g, 81%) as an off-white solid.

Workup

  1. washThe organic layer was washed with 2M sodium hydroxide (3×50 ml), brine (3×50 ml)
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-972057df92844b5f9e0c23d8f9ae6a05
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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