Potassium Carbonate → {3-[4-(4-Dimethylaminomethyltetrahydropyran-4-yl)phenoxy]-propyl}isopropylmethylamine

HRID 272838Notes

Reaction equation

HRID 272838 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]([CH:24]([CH3:26])[CH3:25])[CH3:23].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]([CH:24]([CH3:26])[CH3:25])[CH3:23])=[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 23091614(3-Chloropropyl)(methyl)(propan-2-yl)amineHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol

Product 1

HCID 59837367{3-[4-(4-Dimethylaminomethyltetrahydropyran-4-yl)phenoxy]-propyl}isopropylmethylamineYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (500 mg, 2.13 mmol), (3-chloro-propyl)-isopropyl-methyl-amine (318 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 (96:3:1) provided the title compound (200 mg, 43%) as a white solid. 1H NMR (400 MHz, CDCl3) δ7.20 (d, 2H), 6.87 (d, 2H), 4.00 (t, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 2.83 (sep, 1H), 2.55 (t, 2H), 2.40 (s, 2H), 2.22 (s, 3H), 2.14-2.05 (m, 2H), 1.96 (s, 6H), 2.00-1.82 (m, 4H), 1.00 (d, 6H).

Workup

  1. customPurification by chromatography on silica, eluant DCM:MeOH:NH3 (96:3:1)

Sources & evidence

ORD record
ord-d5a0872bdfba41c78b9279763797969b
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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