Acetic Acid → 4-(1-Methylpiperidin-4-yl)benzoic acid

HRID 2366475Notes

Reaction equation

HRID 2366475 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C=O.[C:18]([BH3-])#N.[Na+].C(O)(=O)C>O.CO>[CH3:18][N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 180024624-(Piperidin-4-yl)benzoic acid

Product 1

HCID 180024554-(1-Methylpiperidin-4-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-piperidin-4-ylbenzoic acid (0.5 g) and 36% formaldehyde in water (0.175 mL) in methanol (5 mL) was treated with sodium cyanoborohydride (0.13 g) and acetic acid (0.5 mL), stirred for 18 hours and concentrated. The concentrate was flash chromatographed on silica gel with 10% methanol/dichloromethane.

Workup

  1. concentrationconcentrated
  2. customchromatographed on silica gel with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-c25f0169937a4962a61a7c007a1e9dcb
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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