1-(3-Chloropropyl)-pyrrolidine → Dimethyl-{4-[3-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-pyran-4-ylmethyl}amine

HRID 272812Notes

Reaction equation

HRID 272812 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1([C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=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][CH2:23]1>>[CH3:3][N:2]([CH3:1])[CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 113210281-(3-Chloropropyl)-pyrrolidineHCID 685763243-{4-[(Dimethylamino)methyl]tetrahydro-pyran-4-yl}phenol

Product 1

HCID 59837505Dimethyl-{4-[3-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-pyran-4-ylmethyl}amine

Procedure

Alkylation of 3-[4-(dimethylamino)methyltetrahydro-2H-pyran-4-yl]phenol (0.1 g, 0.425 mmol) with 1-(3-chloropropyl)pyrrolidine (0.125 g, 0.85 mmol) according to general procedure B gave the desired compound after purification by flash chromatography (0.030 g, 20%). 1H NMR (400 MHz, CDCl3) δ7.27-7.18 (m, 1H), 6.92-6.84 (m, 2H), 6.75 (dd, 1H), 4.05 (t, 2H), 3.8-3.7 (m, 2H), 3.55 (t, 2H), 2.65 (t, 2H), 2.6-2.5 (m, 4H), 2.4 (s, 2H), 2.15-1.85 (m, 6H), 2.0 (s, 6H), 1.85-1.75 (m, 4H).

Sources & evidence

ORD record
ord-f8759ec8d2f44c1385212a1b2f644397
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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