Potassium Carbonate → HCID 59837397, compound

HRID 272826Notes

Reaction equation

HRID 272826 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[CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:3][N:2]([CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]3)=[CH:13][CH:12]=2)[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[CH3:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenolHCID 404243272-[1-(3-Chloropropyl)piperidin-4-yl]ethan-1-ol

Product 1

HCID 59837397HCID 59837397, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (288 mg, 1.22 mmol), 2-[1-(3-chloro-propyl)-piperidin-4-yl]-ethanol (252 mg, 1.22 mmol), DMF (8 ml) and K2CO3 (674 mg, 4.88 mmol) were reacted together according to general procedure B. Purification by chromatography on silica, eluant DCM:MeOH:NH3 (96:4:1) provided the title compound (180 mg, 36%) as an off white solid. 1H NMR (400 MHz, CDCl3) δ7.20 (d, 2H), 6.86 (d, 2H), 3.99 (t, 2H), 3.75 (dt, 2H), 3.70 (t, 2H), 3.55 (td, 2H), 2.98-2.88 (m, 2H), 2.49 (t, 2H), 2.40 (s, 2H), 2.14-1.82 (m, 6H), 1.97 (s, 6H), 1.75-1.15 (m, 10H).

Workup

  1. customPurification by chromatography on silica, eluant DCM:MeOH:NH3 (96:4:1)

Sources & evidence

ORD record
ord-7b0ee31a191e4564bc8f7e1b691187bb
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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