4-Hydroxybenzaldehyde → 4-Piperidin-1-yl methyl-phenol

HRID 456941Notes

Reaction equation

HRID 456941 reaction equation
O[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=[O:18])C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(O)(=O)C>[N:10]1([C:9]2[CH:2]=[CH:3][C:4]([OH:18])=[C:5]([CH3:6])[CH:8]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 200359924-Piperidin-1-yl methyl-phenol

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

A solution of 4-hydroxybenzaldehyde (10 g), piperidine (8.9 mL), and acetic acid (4.7 mL) in DCE (200 mL) was treated with sodium triacetoxyborohydride (24 g). After 16 h, the resulting mixture was treated with saturated aqueous sodium bicarbonate (100 mL) and extracted with DCM (5×100 mL). The combined organic phases were dried (magnesium sulfate) and evaporated. Trituration of the residue with ethyl acetate gave the title compound as a white crystalline solid (5.5 g).

Workup

  1. extractionextracted with DCM (5×100 mL)
  2. dry with materialThe combined organic phases were dried (magnesium sulfate)
  3. customevaporated

Sources & evidence

ORD record
ord-006899123e0349c98a28051f547313ca
Source dataset
uspto-grants-2007_03
Patent number
US07186732B2

Reaction notes

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