Formaldehyde → 1-Methyl-4-piperidinemethanol

HRID 238516

Reaction equation

HRID 238516 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.C=O.[BH3-][C:12]#N.[Na+]>CC#N>[OH:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([CH3:12])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4207714-PiperidinemethanolHCID 5003444Sodium cyanoborohydride

Product 1

HCID 2719711-Methyl-4-piperidinemethanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-piperidylmethanol (1.0 g, 8.7 mmol) and HCHO (2 mL, 25 mmol, 37% in H2O) in CH3CN was added NaCNBH3 (0.5 g, 12.5 mmol). The resulting mixture was stirred for 1 h and filtered. The filtrate was concentrated and the residue was distilled (105° C., 40 torr) to give the title intermediate.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. distillationthe residue was distilled (105° C., 40 torr)

Sources & evidence

ORD record
ord-cbf6007db3ec4fcd92703db4737489df
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Linked notes

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