Potassium Carbonate → N-({4-[4-(3-piperidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)pyridin-2-amine

HRID 273040

Reaction equation

HRID 273040 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][C:9]1([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.Cl.Cl[CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:27]1([CH2:26][CH2:25][CH2:24][O:21][C:18]2[CH:19]=[CH:20][C:15]([C:9]3([CH2:8][NH:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)=[CH:16][CH:17]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 685779444-{4-[(pyridin-2-ylamino)methyl]tetrahydro-2H-pyran-4-yl}phenol

Product 1

HCID 59837516N-({4-[4-(3-piperidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)pyridin-2-amineYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-{4-[(pyridin-2-ylamino)methyl]tetrahydro-2H-pyran-4-yl}phenol (200 mg, 0.704 mmol), 3-chloropropylpiperidine hydrochloride (152 mg, 0.775 mmol) and potassium carbonate (204 mg, 1.48 mmol) were stirred in DMF (1 ml) at 45° C. for 24 hours until complete. The reaction was then partitioned between ethyl acetate (40 ml) and water (40 ml). The organic layer was separated, dried over sodium sulphate and concentrated in vacuo to give a solid. The solid was purified by preparative HPLC to give the title compound (220 mg, 76%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.44-1.55 (m, 2H), 1.64-1.78 (m, 4H), 1.85-2.00 (m, 2H), 2.08-2.18 (m, 4H), 2.52-2.70 (m, 6H), 3.48 (d, 2H), 3.52-3.62 (m, 2H), 3.78-3.85 (m, 2H), 4.02 (t, 2H), 6.21 (d, 1H), 6.50 (t, 1H), 6.90 (d, 2H), 7.24 (d, 2H), 7.34 (t, 1H), 8.01 (d, 1H). LRMS APCI+ m/z 410 [MH]+.

Workup

  1. customThe reaction was then partitioned between ethyl acetate (40 ml) and water (40 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customto give a solid
  6. customThe solid was purified by preparative HPLC

Sources & evidence

ORD record
ord-a2ec25f8de7b45628d549e1838557851
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Linked notes

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