Potassium Carbonate → HCID 59837540, compound

HRID 272829Notes

Reaction equation

HRID 272829 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][O:30][CH3:31])[CH2:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:31][O:30][CH2:29][CH2:28][CH:25]1[CH2:24][CH2:23][N:22]([CH2:21][CH2:20][CH2:19][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)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenolHCID 23091623HCID 23091623, compound

Product 1

HCID 59837540HCID 59837540, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (500 mg, 2.13 mmol), 1-(3-chloro-propyl)-4-(2-methoxy-ethyl)-piperidine (466 mg, 2,13 mmol), DMF (10 ml) and K2CO3 (1.18 g, 8.52 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 (409 mg, 46%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ7.20 (d, 2H), 6.86 (d, 2H), 3.99 (t, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 3.41 (t, 2H), 3.33 (s, 3H), 2.97-2.86 (m, 2H), 2.49 (t, 2H), 2.40 (s, 2H), 2.15-1.78 (m, 8H), 1.97 (s, 6H), 1.74-1.17 (m, 7H).

Workup

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

Sources & evidence

ORD record
ord-5c463513ff04455592a187751bb33f9c
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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