Formaldehyde → HCID 22903531, compound

HRID 1440287Notes

Reaction equation

HRID 1440287 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([CH2:30][CH2:31]N)[C:6]=2[CH:33]=1.C=O.[C:36]([BH3-])#[N:37].[Na+].[C:40](=O)([O-])[O-].[K+].[K+]>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([CH2:30][CH2:31][N:37]([CH3:36])[CH3:40])[C:6]=2[CH:33]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 22903536HCID 22903536, compound

Product 1

HCID 22903531HCID 22903531, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 7-chloro-5-(2-aminoethyl)-1-[6-(2-chlorobenzoyl-amino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.5 g) in methanol (20 ml) is added 37% formalin (1.4 ml), and thereto is added sodium cyanoborohydride (0.2 g), and further thereto is added with stirring acetic acid (0.9 ml) at 10° C., and the mixture is stirred at room temperature for 3 hours. The mixture is poured into ice-water, and the mixture is made basic with potassium carbonate, and the mixture is extracted with dichloromethane. The extract is washed with water, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography to give 7-chloro-5-(2-dimethylaminoethyl)-1-[6-(2-chlorobenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.37 g) as colorless amorphous.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. washThe extract is washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ba44d4eadf5144c0a94d3c7464062890
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

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