4-Bromobutyronitrile → 4-(2-Chloro-3-piperidinomethylphenoxy)butyronitrile

HRID 35597

Reaction equation

[Cl:1][C:2]1[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.Br[CH2:17][CH2:18][CH2:19][C:20]#[N:21]>>[Cl:1][C:2]1[C:3]([CH2:4][N:5]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:11][CH:12]=[CH:13][C:14]=1[O:15][CH2:17][CH2:18][CH2:19][C:20]#[N:21]

Participants

Reactant 2

HCID 214124-Bromobutyronitrile

HCID 21294597N-(2-chloro-3-hydroxybenzyl)piperidine

Product 1

HCID 212945534-(2-Chloro-3-piperidinomethylphenoxy)butyronitrile

Procedure

In a similar manner to that described in Example 17 2-chloro-3-hydroxybenzaldehyde (9 g) in absolute ethanol (60 ml) was treated with piperidine (11.7 ml) and sodium borohydride (2.2 g) to yield N-(2-chloro-3-hydroxybenzyl)piperidine. The piperidine thus prepared was reacted with 4-bromobutyronitrile to give 4-(2-chloro-3-piperidinomethylphenoxy)butyronitrile.

Sources & evidence

ORD record: ord-83f7587f3fc4437aabe7bd529e5d8791
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04767769

Linked notes

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