Ammonia → Dimethyl-(4-{4-[3-(2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-tetrahydro-pyran-4-ylmethyl)-amine

HRID 272815Notes

Reaction equation

HRID 272815 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[CH2:26][CH2:25][CH2:24][CH:23]1[CH3:27].C([O-])([O-])=O.[K+].[K+].N>CO.C(Cl)Cl.CN(C=O)C>[CH3:3][N:2]([CH3:1])[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[CH2:26][CH2:25][CH2:24][CH:23]3[CH3:27])=[CH:13][CH:12]=2)[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 125732671-(3-Chloro-propyl)-2-methyl-pyrrolidineHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol

Product 1

HCID 23091679Dimethyl-(4-{4-[3-(2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-tetrahydro-pyran-4-ylmethyl)-amineYield 16%

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-methyl-pyrrolidine (344 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 (120 mg, 16%). 1H NMR (400 MHz, CDCl3) δ7.20 (d, 2H), 6.87 (d, 2H), 4.08-3.96 (m, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 3.18 (td, 1H), 2.98 (m, 1H), 2.40 (s, 2H), 2.29 (m, 1H), 2.20 (m, 1H), 2.16-1.62 (m, 10H), 1.96 (s, 6H), 1.42 (m, 1H), 1.09 (d, 3H).

Sources & evidence

ORD record
ord-49d21f0d29dc4d1eb3d425bf8dc882f5
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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