4-Hydroxybenzaldehyde → 4-Piperidin-1-ylmethyl-phenol

HRID 1790010Notes

Reaction equation

HRID 1790010 reaction equation
[OH:1][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)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(O)(=O)C>[N:10]1([CH2:6][C:5]2[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=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 116369724-Piperidin-1-ylmethyl-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-bb490914043a4089a4b4985a7be43596
Source dataset
uspto-grants-2006_07
Patent number
US07071191B2

Reaction notes

Loading…