Formaldehyde → HCID 89500552, compound

HRID 2178526Notes

Reaction equation

HRID 2178526 reaction equation
[CH3:1][Si:2]([CH2:5][NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=[O:21])([CH3:4])[CH3:3].[CH3:22]O.C=O.[C:26](=[O:29])([O-])[O-].[K+].[K+]>ClCCl>[CH3:22][O:29][CH2:26][N:6]([CH2:5][Si:2]([CH3:3])([CH3:4])[CH3:1])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=[O:21]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 11430Potassium CarbonateHCID 89500295HCID 89500295, compound

Product 1

HCID 89500552HCID 89500552, compoundYield 223.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-[2-(2-{[(Trimethylsilyl)methyl]amino}ethyl)phenyl]piperidin-2-one a5-1 (912 mg, 3 mmol, 1 eq) is slowly added at −10° C. to a solution of methanol (220 μl, 5.4 mmol, 1.8 eq) and aqueous formaldehyde (37%, 600 μl). The reaction mixture is stirred at 0° C. for 1 h. Potassium carbonate (2 g) is added and the mixture is stirred 1 h at 0° C. Dichloromethane (15 ml) is added, the mixture obtained is dried over MgSO4, filtered, and the filtrate is concentrated under vacuum to afford 2.34 g of 1-[2-(2-{(methoxymethyl)[(trimethylsilyl)methyl]amino}ethyl)phenyl]piperidin-2-one a5-2.

Workup

  1. stirringthe mixture is stirred 1 h at 0° C
  2. customthe mixture obtained
  3. dry with materialis dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-be13bdc237c34b8583d3a5880fdb4cda
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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