Piperidine → N-(2-chloro-3-hydroxybenzyl)piperidine

HRID 35596

Reaction equation

HRID 35596 reaction equation
[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 5933762-Chloro-3-hydroxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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-a40479b1925649b88b9ca5b70f57c52c
Source dataset
uspto-grants-1988_08
Patent number
US04767769

Linked notes

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