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Dimethylamine → HCID 19599959, compound

HRID 611218
Notes
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Reaction equation

HRID 611218 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:19][CH2:18][CH2:17][C:16]3[CH:20]=[CH:21][O:22][C:15]=3[CH2:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23][NH:24][CH3:25].[CH2:26]=O>C(O)(=O)C>[CH3:23][N:24]([CH2:26][C:21]1[O:22][C:15]2[CH2:14][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:19][CH2:18][CH2:17][C:16]=2[CH:20]=1)[CH3:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 19600068HCID 19600068, compound

Product 1

HCID 19599959HCID 19599959, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.945 g (3.18 mmol) of 7-(6-phenylhexyl)-5,6,7,8-tetrahydro-4H-furo[2,3-c]azepine in 20 ml of acetic acid, 0.34 g (3.8 mmol) of 50% aqueous dimethylamine and 0.31 g (3.8 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 30 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-699e29b8c73642d0abd4490344a00c80
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05998433

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes