Ammonia → (4-{4-[3-(2,6-Dimethylpiperidin-1-yl)propoxy]phenyl}tetra-hydro-pyran-4-ylmethyl)dimethyl-amine

HRID 272816Notes

Reaction equation

HRID 272816 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[C@H:27]([CH3:28])[CH2:26][CH2:25][CH2:24][C@@H:23]1[CH3:29].C([O-])([O-])=O.[K+].[K+].N>CO.C(Cl)Cl.CN(C=O)C>[CH3:29][CH:23]1[CH2:24][CH2:25][CH2:26][CH:27]([CH3:28])[N:22]1[CH2:21][CH2:20][CH2:19][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:5]2([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 12923591cis-1-(3-Chloropropyl)-2,6-dimethylpiperidineHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol

Product 1

HCID 68577028(4-{4-[3-(2,6-Dimethylpiperidin-1-yl)propoxy]phenyl}tetra-hydro-pyran-4-ylmethyl)dimethyl-amineYield 33.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (500 mg, 2.13 mmol), 1-(3-chloro-propyl)-2,6-cis-dimethyl-piperidine (410 mg, 2,13 mmol), DMF (10 ml) and K2CO3 (1.18 g, 8.52 mmol) were reacted together according to general procedure B. The isolated material was subjected to chromatography on silica, eluant 95:4:1 (DCM, MeOH, NH3) to give the title compound as a yellow oil (280 mg, 33.9%). 1H NMR (400 MHz, CDCl3) δ7.20 (d, 2H), 6.85 (d, 2H), 3.93 (t, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 2.95 (t, 2H), 2.51-2.36 (m, 2H), 2.40 (s, 2H), 2.14-2.04 (m, 2H), 1.96 (s, 6H), 1.93-1.82 (m, 4H), 1.74-1.51 (m, 3H), 1.41-1.21 (m, 3H), 1.13 (d, 6H).

Sources & evidence

ORD record
ord-a1ed0cdeeb3f4c828afd68d8a68e63e7
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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