2-(2-Hydroxyphenyl)acetonitrile → [2-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-acetonitrile

HRID 1866544Notes

Reaction equation

HRID 1866544 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].Cl[CH2:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>>[N:15]1([CH2:14][CH2:13][CH2:12][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][C:9]#[N:10])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 105828242-(2-Hydroxyphenyl)acetonitrileHCID 113210281-(3-Chloropropyl)-pyrrolidine

Product 1

HCID 57978244[2-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-acetonitrileYield 58%

Procedure

The title compound was prepared from 2-hydroxy-benzeneacetonitrile (J. Org. Chem.; 66, 3435; 2001) and 1-(3-chloropropyl)pyrrolidine, using a method similar to that of preparation 104, as a pale brown gum in 58% yield. 1H NMR (400 MHz, CD3OD) δ: 7.33-7.25 (2H, m), 7.02-6.90 (2H, m), 4.12-4.09 (2H, m), 3.75 (2H, s), 2.76-2.72 (2H, m), 2.62-2.57 (4H, m), 2.09-2.02 (2H, m), 1.87-1.78 (4H, m); LRMS APCI m/z 245 [M+H]+

Workup

  1. customof preparation 104

Sources & evidence

ORD record
ord-52e5908a3e544508ac862e3188228f8e
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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