Formaldehyde → HCID 22903519, compound

HRID 1440279Notes

Reaction equation

HRID 1440279 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:32])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:31])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][CH2:29]N)=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][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>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:32])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:31])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][CH2:29][N:37]([CH3:36])[CH3:40])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:33]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 22903484HCID 22903484, compound

Product 1

HCID 22903519HCID 22903519, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 7-chloro-1-{6-[2-(2-aminoethoxy)benzoylamino]-nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.11 g) in methanol (3 ml) is added 37% formalin (0.24 ml), and thereto is added sodium cyanoborohydride (0.044 g), and thereto is added with stirring acetic acid (0.18 ml) at 10° C. The mixture is stirred at room temperature for one hour, and poured into ice-water, and the mixture is made basic with potassium carbonate, and 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, and the resultant is dissolved in ethanol (5 ml), and thereto is added conc. hydrochloric acid, and the mixture is stirred at room temperature for one hour. The mixture is evaporated under reduced pressure to remove the solvent, and crystallized from diethyl ether to give 7-chloro-1-{6-[2-(2-dimethylaminoethoxy)benzoyl-amino]nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine dihydrochloride (53 mg) as white powder.

Workup

  1. extractionextracted 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
  7. dissolutionthe resultant is dissolved in ethanol (5 ml)
  8. additionis added conc. hydrochloric acid
  9. stirringthe mixture is stirred at room temperature for one hour
  10. customThe mixture is evaporated under reduced pressure
  11. customto remove the solvent
  12. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-2b8aa7864c3e4a40a0c6d1146f51ca24
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

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