Formaldehyde → HCID 53765784, compound

HRID 2288977Notes

Reaction equation

HRID 2288977 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[O:29])[NH:18][CH2:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[O:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30](=O)(O)[O-:31].[Na+].C=O>O.CS(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17](=[O:29])[NH:18][CH:19]([CH2:30][OH:31])[C:20]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[O:21])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 53700144HCID 53700144, compound

Product 1

HCID 53765784HCID 53765784, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of the 4-[2-(4-chlorophenyl)-2-oxo-ethylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (8.91 g, 21.5 mmol), prepared as in Part B, and sodium bicarbonate (0.19 g, 2.3 mmol) in a mixture of water (10 mL) and dimethyl sulfoxide (50 mL) in a 50° C. water bath is added aqueous formaldehyde (3.30 mL, 44.0 mmol). After 6 h, the mixture is diluted with water (1 L) and allowed to stand overnight at RT. Filtration gives gummy solids which are triturated with ethyl acetate to give the desired product as white solids.

Workup

  1. waitto stand overnight at RT
  2. filtrationFiltration
  3. customgives gummy solids which
  4. customare triturated with ethyl acetate

Sources & evidence

ORD record
ord-64c3a2e4034846cb98be5eb96797f1bb
Source dataset
uspto-grants-2000_07
Patent number
US06090825

Reaction notes

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