Formaldehyde → 4-(4-Bromobenzyl)-1-methylpiperidine

HRID 1505865Notes

Reaction equation

HRID 1505865 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[CH2:15]=O>C(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([CH3:15])[CH2:11][CH2:12]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 20689421HCID 20689421, compound

Product 1

HCID 582668454-(4-Bromobenzyl)-1-methylpiperidineYield 98.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-(4-bromobenzyl)-piperidine (290 mg, 1.14 mmol), formic acid (12 mL) and 37% aqueous formaldehyde (0.30 mL, 3.75 mmol) was divided into three portions. Each portion was heated at 150° C. for 5 minutes in a microwave reactor. The combined cold mixture was loaded onto a 5 g SCX-2 cartridge which was then washed with methanol (30 mL) then 2 N ammonia in methanol (50 mL). Concentration of the combined basic fractions in vacuo gave the title compound (300 mg, 98%) as a colourless oil. LCMS (Method B): RT=2.18 min, M+H+=268, 270.

Workup

  1. washwas then washed with methanol (30 mL)

Sources & evidence

ORD record
ord-7ee188f646ee48cbb00f0d5717a3ed76
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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