Ethanol → HCID 54140787, compound

HRID 2288956Notes

Reaction equation

HRID 2288956 reaction equation
[O:1]=[C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10]([C:13](=[O:15])[CH3:14])[CH2:9][CH2:8]1)=[O:6].C[CH2:23][OH:24].C=O>O>[OH:24][CH2:23][CH:3]([NH:4][C:5]([CH:7]1[CH2:8][CH2:9][N:10]([C:13](=[O:15])[CH3:14])[CH2:11][CH2:12]1)=[O:6])[C:2](=[O:1])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 712FormaldehydeHCID 54189816HCID 54189816, compound

Product 1

HCID 54140787HCID 54140787, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 1-Acetyl-piperidine-4-carboxylic acid (2-oxo-2-phenyl-ethyl)-amide (40.66 g, 141 mmol), prepared as in Intermediate 2A, in 2:1 EtOH: H2O (160 mL EtOH, 80 mL H2O) is treated with 37% aqueous formaldehyde (21.1 mL, 282 mmol) and NaCHO3 (1.18 g, 14.1 mmol). The reaction mixture is stirred at 23° C. for 6 h, and the resulting precipitate is removed by filtration. The filtrate is cooled to 0° C. and diluted with H2O (100 mL), and a second crop of 1-Acetyl-piperidine-4-carboxylic acid (1-hydroxymethyl-2-oxo-2-phenyl-ethyl)-amide is obtained by filtration.

Workup

  1. customthe resulting precipitate is removed by filtration
  2. temperatureThe filtrate is cooled to 0° C.
  3. additiondiluted with H2O (100 mL)

Sources & evidence

ORD record
ord-a78564fdbc87478fa623fa830c296a49
Source dataset
uspto-grants-2000_07
Patent number
US06090825

Reaction notes

Loading…