Formaldehyde → HCID 13755079, compound

HRID 2309191Notes

Reaction equation

HRID 2309191 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:13]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[C:7]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8]2.[CH2:19]=O.[BH4-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:13]2[CH2:18][CH2:17][CH2:16][N:15]([CH3:19])[CH2:14]2)=[C:7]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8]2

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 13755077HCID 13755077, compound

Product 1

HCID 13755079HCID 13755079, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

4.5 g of the product of Example 1 were dissolved in 100 ml of methanol with stirring under an inert atmosphere and after cooling to about 5° C., 3.4 ml of 40% formic aldehyde were added dropwise. After stirring for 1 hour, 1.8 g of 95% sodium borohydride were added in small fractions and the mixture was stirred for 1 hour. The temperature was allowed to return to ambient and after diluting with iced water, extracting with methylene chloride, drying and evaporating to dryness under reduced pressure, filtering, washing with ether and drying, 4 g of 1,3-dihydro-7-methoxy-4-(1-methyl-3-piperidinyl)-2H-indol-2-one were obtained in the form of a base melting at ≃170° C.

Workup

  1. stirringAfter stirring for 1 hour
  2. stirringthe mixture was stirred for 1 hour
  3. extractionextracting with methylene chloride
  4. customdrying
  5. customevaporating to dryness under reduced pressure
  6. filtrationfiltering
  7. washwashing with ether
  8. customdrying

Sources & evidence

ORD record
ord-af3574abc65b4b5cae45c2d7b6f2f9cc
Source dataset
uspto-grants-1987_09
Patent number
US04694011

Reaction notes

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