4-(Aminomethyl)piperidine → 4-bromo-2-[N-(4-piperidylmethyl)iminomethyl]phenol

HRID 1584870Notes

Reaction equation

HRID 1584870 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=O.[NH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:7]=[N:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:9]=1

Participants

4

Reactant 2

HCID 235274-(Aminomethyl)piperidineHCID 728635-Bromosalicylaldehyde

Product 1

HCID 1354507774-bromo-2-[N-(4-piperidylmethyl)iminomethyl]phenolYield 106.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-bromo-2-hydroxybenzaldehyde (170 g) and 4-(aminomethyl)piperidine (96.9 g) in ethanol (2.5 L) was stirred at ambient temperature for 3 hours. The solvent was removed in vacuo to give 4-bromo-2-[N-(4-piperidylmethyl)iminomethyl]phenol (267 g) as a yellow solid m.p 35-38° C.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b36ecda2af7d4a1a892ac9f922dcf031
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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