Dimethylamine → HCID 19600001, compound

HRID 611082Notes

Reaction equation

HRID 611082 reaction equation
[CH2:1]([CH:8]1[NH:13][CH2:12][C:11]2[CH:14]=[CH:15][O:16][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][NH:18][CH3:19].[CH2:20]=O>C(O)(=O)C>[CH3:17][N:18]([CH2:20][C:15]1[O:16][C:10]2[CH2:9][CH:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[NH:13][CH2:12][C:11]=2[CH:14]=1)[CH3:19]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 19599971HCID 19599971, compound

Product 1

HCID 19600001HCID 19600001, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1.030 g (4.829 mmol) of 6-benzyl-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 30 ml of acetic acid, 0.52 g (5.80 mmol) of 50% aqueous dimethylamine and 0.47 g (5.80 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 15 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1) to yield the desired product.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1)

Sources & evidence

ORD record
ord-04650e36531c440da9f6c47930008b44
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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