Formaldehyde → HCID 136104190, compound

HRID 2088681Notes

Reaction equation

HRID 2088681 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[C:10]1[NH:15][C:14](=[O:16])[N:13]2[N:17]=[C:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[N:19]=[C:12]2[CH:11]=1.[CH2:26]=O.[Na]>CO>[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[C:10]1[NH:15][C:14](=[O:16])[N:13]2[N:17]=[C:18]([CH:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[N:19]=[C:12]2[CH:11]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5360545SodiumHCID 1363378137-(2,4-Dichlorophenyl)-2-(piperidin-4-yl)[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one hydrochloride

Product 1

HCID 136104190HCID 136104190, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 500 mg (1.25 mmol) of 7-(2,4-dichlorophenyl)-2-(piperidin-4-yl)[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one hydrochloride were initially charged in methanol (4 ml), and 3 Å molecular sieve (50 mg), formalin (210 μl, 7.50 mmol) and sodium cyanoborhydride (470 mg, 7.50 mmol) were added. The mixture was stirred at 0° C. for 1 h and then stirred at RT for another 12 h. The reaction mixture was filtered, and dichloromethane (100 ml) and water (75 ml) were added to the filtrate. The mixture was extracted and the organic phase was dried (magnesium sulfate) and concentrated. This gave 274 mg (58% of theory) of the crude product.

Workup

  1. stirringstirred at RT for another 12 h
  2. filtrationThe reaction mixture was filtered
  3. additiondichloromethane (100 ml) and water (75 ml) were added to the filtrate
  4. extractionThe mixture was extracted
  5. dry with materialthe organic phase was dried (magnesium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cc6d963ed1b94c74979317a8cfd2b01f
Source dataset
uspto-grants-2013_05
Patent number
US08436003B2

Reaction notes

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