Ammonia → (4-{4-[3-(2,5-Dimethylpyrrolidin-1-yl)propoxy]phenyl}tetra-hydro-pyran-4-ylmethyl)dimethylamine

HRID 272813Notes

Reaction equation

HRID 272813 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:26]([CH3:27])[CH2:25][CH2:24][C@@H:23]1[CH3:28].C([O-])([O-])=O.[K+].[K+].N>CO.C(Cl)Cl.CN(C=O)C>[CH3:28][CH:23]1[CH2:24][CH2:25][CH:26]([CH3:27])[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 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenolHCID 685770241-(3-Chloro-propyl)-2,5-trans-dimethyl-pyrrolidine

Product 1

HCID 68581270(4-{4-[3-(2,5-Dimethylpyrrolidin-1-yl)propoxy]phenyl}tetra-hydro-pyran-4-ylmethyl)dimethylamineYield 38.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (330 mg, 1.43 mmol), 1-(3-chloro-propyl)-2,5-trans-dimethyl-pyrrolidine (221 mg, 1.26 mmol), DMF (7.6 ml) and K2CO3 (790 mg, 5.72 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 (180 mg, 34%). 1H NMR (400 MHz, CDCl3) δ7.20 (d, 2H), 6.87 (d, 2H), 4.08-3.95 (m, 2H), 3.79-3.70 (m, 2H), 3.59-3.49 (m, 2H), 3.11-3.00 (m, 2H), 2.77 (m, 1H), 2.54 (m, 1H), 2.40 (s, 2H), 2.14-1.81 (m, 8H), 1.96 (s, 6H), 1.44-1.31 (m, 2H), 0.97 (d, 6H).

Sources & evidence

ORD record
ord-adba8e2f261e4253b92822850a340496
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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