3-Hydroxybenzaldehyde → 3-[(3-Methylpiperidin-1-yl)methyl]phenol

HRID 4648

Reaction equation

HRID 4648 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][CH:11]1[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]1.C(O)=O.N>O>[CH3:10][CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([CH2:5][C:4]2[CH:3]=[C:2]([OH:1])[CH:9]=[CH:8][CH:7]=2)[CH2:12]1

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 222AmmoniaHCID 284Formic AcidHCID 790813-Methylpiperidine

Product 1

HCID 133646663-[(3-Methylpiperidin-1-yl)methyl]phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

24.4 g (0.2 mol) of 3-hydroxybenzaldehyde are mixed with 40 ml (about 0.4 mol) of 3-methylpiperidine and 20 ml (about 0.52 mol) of 100% formic acid with cooling and then stirred for 2 hours at 120° C. When the reaction mixture has cooled to room temperature, it is poured into water and rendered alkaline with ammonia, and the precipitated solid is filtered off and recrystallised from ethanol.

Workup

  1. temperaturewith cooling
  2. temperatureWhen the reaction mixture has cooled to room temperature
  3. filtrationthe precipitated solid is filtered off
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-e9c53b21b5524c4296badbb52530d5b3
Source dataset
uspto-grants-1988_02
Patent number
US04727081

Linked notes

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