Potassium Carbonate → (S)-N-[1-(4-{1-[4-(Tetrahydro-2H-pyran-4-yloxy)-phenyl]-piperidin-4-yl}-phenyl)-ethyl]-acetamide

HRID 1470751Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][CH2:5][CH3:6].[C:7]([O-])([O-])=O.[K+].[K+].[OH:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][CH:23]([C:26]3[CH:31]=[CH:30][C:29]([C@@H:32]([NH:34][C:35](=[O:37])[CH3:36])[CH3:33])=[CH:28][CH:27]=3)[CH2:22][CH2:21]2)=[CH:16][CH:15]=1>C(#N)C>[O:4]1[CH2:5][CH2:6][CH:7]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([C:26]4[CH:27]=[CH:28][C:29]([C@@H:32]([NH:34][C:35](=[O:37])[CH3:36])[CH3:33])=[CH:30][CH:31]=4)[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

17 μL (0.15 mmol) 1-Bromo-2-ethoxy-ethane and 35 mg (0.25 mmol) K2CO3 are added to 34 mg (0.10 mmol) (S)-N-{1-(4-[1-(4-hydroxyphenyl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide (compound 1.48) in 2 mL ACN. The mixture is stirred at 90° C. for 4 h followed by addition of 11 μL (0.10 mmol) 1-bromo-2-ethoxy-ethane. Stirring is continued at 90° C. over night. The solvent is removed in vacuo and the residue is purified using reversed phase HPLC (water/MeOH, 0.1% TFA) to yield the desired product.

Workup

stirringStirring
waitis continued at 90° C. over night
customThe solvent is removed in vacuo
customthe residue is purified

Sources & evidence

ORD record: ord-eb6de40abcff4abea51245ce6849725d
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006450B2

Reaction notes

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