Acetaldehyde → HCID 21497569, compound

HRID 1730406Notes

Reaction equation

HRID 1730406 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:15][NH2:16])=[CH:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]=2[CH:23]=1.[CH:24](=O)[CH3:25].C([BH3-])#N.[Na+].[C:31](#N)[CH3:32]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:15][N:16]([CH2:24][CH3:25])[CH2:31][CH3:32])=[CH:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]=2[CH:23]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 6342Acetonitrile2×HCID 5003444Sodium cyanoborohydrideHCID 12707088HCID 12707088, compound

Product 1

HCID 21497569HCID 21497569, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 8-chloro-1-(aminomethyl)-6-phenyl-4H-imidazo[1,2-a][1,4]benzodiazepine (1.42 g, 4.3 mmole) in 20 ml. of acetonitrile under nitrogen is treated successively with acetaldehyde (1.5 ml) and sodium cyanoborohydride (NaBH3CN) (550 mg). This mixture is treated dropwise, with a solution of 0.2 ml of acetic acid in 2 ml. of acetonitrile over a period of 1 hour and 30 minutes. [The addition is continued until the pH of the reaction mixture is between 6.4 - 6.8]. The mixture is stirred for 15 minutes at ambient temperature and concentrated in vacuo. The residue is treated with cold water saturated with sodium chloride and extracted with chloroform (5- ml., 3X). The chloroform solution is washed with water and saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated in vacuo to give a yellow oil. This oil is chromatographed over silica gel by eluting with 2% methanol-98% chloroformmixtures to afford 8-chloro-1-[(diethylamino)methyl]-6-phenyl-4H-imidazo[1,2-a][1,4]benzodiazepine.

Workup

  1. custom30 minutes
  2. addition[The addition
  3. concentrationconcentrated in vacuo
  4. additionThe residue is treated with cold water saturated with sodium chloride
  5. extractionextracted with chloroform (5- ml., 3X)
  6. washThe chloroform solution is washed with water and saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a yellow oil
  10. customThis oil is chromatographed over silica gel
  11. washby eluting with 2% methanol-98% chloroformmixtures

Sources & evidence

ORD record
ord-7603511fb5f4443fbf073ec34ec44046
Source dataset
uspto-grants-1976_11
Patent number
US03992408

Reaction notes

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