4-{3-[(Piperidin-1-yl)methyl]phenoxy}butanenitrile → 4-(3-Piperidinomethylphenoxy)butaneamine

HRID 1710089Notes

Reaction equation

HRID 1710089 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[O:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 197625514-{3-[(Piperidin-1-yl)methyl]phenoxy}butanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 137906124-(3-Piperidinomethylphenoxy)butaneamineYield 97.3%

Procedure

In a similar manner to that of Example 16 (ii) reaction of 4-[3-(piperidinomethyl)phenoxy]butyronitrile (2.58 g) and lithium aluminium hydride (0.46 g) gave 4-[3-(piperidinomethyl)phenoxy]butylamine (2.55 g) as an oil. This oil and 2-chlorobenzthiazole (1.81 g) were fused at 130° C. for 4 hours. The cooled residue was subjected to column chromatography on silica using dichloromethane:methanol:ammonium hydroxide (90:5:05) as eluant to give the title compound (1.6 g), m.p. 92°-93° C. (recrystallised from toluene).

Sources & evidence

ORD record
ord-e89a9073aa5f44aa919898f98b42da31
Source dataset
uspto-grants-1990_08
Patent number
US04952589

Reaction notes

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