Piperidine → N-(2-chloro-5-hydroxybenzyl)piperidine

HRID 35595Notes

Reaction equation

HRID 35595 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([O:6]CCCC#N)=[CH:4][C:3]=1[CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.ClC1C=CC(O)=CC=1C=O.N1CCCCC1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([OH:6])=[CH:4][C:3]=1[CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 4311764Sodium borohydrideHCID 212945242-Chloro-5-hydroxybenzaldehydeHCID 212945694-(4-Chloro-3-piperidinomethylphenoxy)butyronitrile

Product 1

HCID 21294588N-(2-chloro-5-hydroxybenzyl)piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar manner to that described in Example 17 4-(4-chloro-3-piperidinomethylphenoxy)butyronitrile was prepared by the reaction of 2-chloro-5-hydroxybenzaldehyde (1.379 g), piperidine (1.8 ml) and sodium borohydride (0.33 g) in absolute ethanol (10 ml) to produce N-(2-chloro-5-hydroxybenzyl)piperidine which was then reacted with 4-bromobutyronitrile to yield the above-mentioned product.

Sources & evidence

ORD record
ord-95815a52177f4c3bb8ffeaa4ad63dff2
Source dataset
uspto-grants-1988_08
Patent number
US04767769

Reaction notes

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