Piperidine → N-(5-hydroxy-2-nitrobenzyl)piperidine

HRID 35594

Reaction equation

HRID 35594 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8]CCCC#N)=[CH:6][C:5]=1[CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)([O-:3])=[O:2].OC1C=CC([N+]([O-])=O)=C(C=1)C=O.N1CCCCC1.[BH4-].[Na+]>C(O)C>[OH:8][C:7]1[CH:14]=[CH:15][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([CH:6]=1)[CH2:16][N:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 4311764Sodium borohydrideHCID 212945394-(4-Nitro-3-piperidinomethylphenoxy)butyronitrile

Product 1

HCID 21294596N-(5-hydroxy-2-nitrobenzyl)piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar manner to that described in Example 17 4-(4-nitro-3-piperidinomethylphenoxy)butyronitrile was prepared by the reaction of 5-hydroxy-2-nitrobenzaldehyde (10 g) with piperidine (12.3 ml) and sodium borohydride (2.7 g) in absolute ethanol (68 ml) to give N-(5-hydroxy-2-nitrobenzyl)piperidine which was then reacted with 4-bromobutyronitrile (4.1 ml) to give the above-mentioned product.

Sources & evidence

ORD record
ord-4c69cf8838334333a8e1c9f9c441adb5
Source dataset
uspto-grants-1988_08
Patent number
US04767769

Linked notes

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